Organic Reactions, Volume 93 E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Serie: Organic Reactions
• Sprache: Englisch

Seitenzahl: 214

Veröffentlichungsjahr: 2017

Beschreibung

The latest volume in this series for organic chemists in industry presents critical discussions of widely used organic reactions or particular phases of a reaction. The material is treated from a preparative viewpoint, with emphasis on limitations, interfering influences, effects of structure and the selection of experimental techniques. The work includes tables that contain all possible examples of the reaction under consideration. Detailed procedures illustrate the significant modifications of each method.

Leseprobe

Table of Contents

Cover

Title Page

Copyright

Introduction to the Series Roger Adams, 1942

Introduction to the Series Scott E. Denmark, 2008

Preface to Volume 93

Chapter 1: Enantioselective, Rhodium-Catalyzed 1,4-Addition of Organoboron Reagents to Electron-Deficient Alkenes

Acknowledgments

Introduction

Mechanism and Stereochemistry

Scope and Limitations

Applications to Synthesis

Comparison With Other Methods

Experimental Conditions

Experimental Procedures

Tabular Survey

References

Cumulative Chapter Titles by Volume

Author Index, Volumes 1–93

Chapter and Topic Index, Volumes 1–93

End User License Agreement

Pages

v

vi

vii

viii

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195

196

197

198

199

200

201

202

203

204

205

206

207

208

209

210

211

212

213

214

215

216

217

218

219

220

221

222

223

224

225

226

227

228

229

230

231

232

233

234

235

236

237

238

239

240

241

242

243

244

245

246

247

248

249

250

251

252

253

254

255

256

257

258

259

260

261

262

263

264

265

266

267

268

269

270

271

272

273

274

275

276

277

278

279

280

281

282

283

284

285

286

287

288

289

290

291

292

293

294

295

296

297

298

299

300

301

302

303

304

305

306

307

308

309

310

311

312

313

314

315

316

317

318

319

320

321

322

323

324

325

326

327

328

329

330

331

332

333

334

335

336

337

338

339

340

341

342

343

344

345

346

347

348

349

350

351

352

353

354

355

356

357

358

359

360

361

362

363

364

365

366

367

368

369

370

371

372

373

374

375

376

377

378

379

380

381

382

383

384

385

386

387

388

389

390

391

392

393

394

395

396

397

398

399

400

401

402

403

404

405

406

407

408

409

410

411

412

413

414

415

416

417

418

419

420

421

422

423

424

425

426

427

428

429

430

431

432

433

434

435

436

437

438

439

440

441

442

443

444

445

446

447

448

449

450

451

452

453

454

455

456

457

458

459

460

461

462

463

464

465

466

467

468

469

470

471

472

473

474

475

476

477

478

479

480

481

482

483

484

485

486

487

488

489

490

491

492

493

494

495

496

497

498

499

500

501

502

503

504

505

506

507

508

509

510

511

512

513

514

515

516

517

518

519

520

521

522

523

524

525

526

527

528

529

530

531

532

533

534

535

536

537

538

539

540

541

542

543

544

545

546

547

548

549

550

551

552

553

554

555

556

557

558

559

560

561

562

563

564

565

566

567

568

569

570

571

572

573

574

575

576

577

578

579

580

581

582

583

584

585

586

587

588

589

590

591

592

593

594

595

596

597

598

599

600

601

602

603

604

605

606

607

608

609

610

611

612

613

614

615

616

617

618

619

620

621

622

623

624

625

626

627

628

629

630

631

632

633

634

635

636

637

638

639

640

641

642

643

644

645

646

647

648

649

650

651

652

653

654

655

656

657

658

659

660

661

662

663

664

665

666

667

668

669

670

671

672

673

674

675

676

677

678

679

680

681

682

683

684

685

686

687

688

689

690

691

692

693

694

695

696

697

698

699

700

701

702

703

705

706

707

708

709

710

711

712

713

714

715

716

717

718

719

720

721

722

723

724

725

726

Guide

Cover

Table of Contents

Preface to Volume 93

Begin Reading

List of Illustrations

Chapter 1: Enantioselective, Rhodium-Catalyzed 1,4-Addition of Organoboron Reagents to Electron-Deficient Alkenes

Scheme 1

Scheme 2

Scheme 3

Scheme 4

Scheme 5

Scheme 6

Scheme 7

Scheme 8

Scheme 9

Figure 1 Organoboron reagents employed in enantioselective Rh-catalyzed 1,4-additions.

Scheme 10

Scheme 11

Scheme 12

Scheme 13

Scheme 14

Scheme 15

Scheme 16

Scheme 17

Scheme 18

Scheme 19

Scheme 20

Scheme 21

Scheme 22

Scheme 23

Scheme 24

Scheme 25

Scheme 26

Scheme 27

Scheme 28

Scheme 29

Scheme 30

Scheme 31

Scheme 32

Scheme 33

Scheme 34

Scheme 35

Scheme 36

Scheme 37

Scheme 38

Scheme 39

Scheme 40

Scheme 41

Scheme 42

Scheme 43

Scheme 44

Scheme 45

Scheme 46

Scheme 47

Scheme 48

Scheme 49

Scheme 50

Scheme 51

Scheme 52

Scheme 53

Scheme 54

Scheme 55

Scheme 56

Scheme 57

Scheme 58

Scheme 59

Scheme 60

Scheme 61

Scheme 62

Scheme 63

Scheme 64

Scheme 65

Scheme 66

Scheme 67

Scheme 68

Scheme 69

Scheme 70

Scheme 71

Scheme 72

Scheme 73

Scheme 74

Scheme 75

Scheme 76

Scheme 77

Scheme 78

Scheme 79

Scheme 80

Scheme 81

Scheme 82

Scheme 83

Scheme 84

Scheme 85

Scheme 86

Scheme 87

Scheme 88

Scheme 89

Scheme 90

Scheme 91

Scheme 92

Scheme 93

Scheme 94

Scheme 95

Scheme 96

Scheme 97

Scheme 98

Scheme 99

Scheme 100

Scheme 101

Scheme 102

Scheme 103

Scheme 104

Scheme 105

Scheme 106

Scheme 107

Scheme 108

Scheme 109

Scheme 110

Scheme 111

Scheme 112

Scheme 113

Scheme 114

Scheme 115

Scheme 116

Scheme 117

Scheme 118

Scheme 119

Scheme 120

Scheme 121

Scheme 122

Scheme 123

Scheme 124

Scheme 125

Scheme 126

Scheme 127

Scheme 128

Scheme 129

Scheme 130

Scheme 131

Scheme 132

Scheme 133

Scheme 134

Scheme 135

Scheme 136

Scheme 137

Scheme 138

Scheme 139

Scheme 140

Scheme 141

Scheme 142

Scheme 143

Scheme 144

Scheme 145

Scheme 146

Scheme 147

Scheme 148

Scheme 149

Scheme 150

Scheme 151

Scheme 152

Scheme 153

Scheme 154

Scheme 155

Scheme 156

Scheme 157

Scheme 158

Scheme 159

Scheme 160

Scheme 161

Scheme 162

Scheme 163

Scheme 164

Scheme 165

Scheme 166

List of Tables

Chapter 1: Enantioselective, Rhodium-Catalyzed 1,4-Addition of Organoboron Reagents to Electron-Deficient Alkenes

Table 1A. Reactions of α, β-Unsaturated Ketones with Arylboron Reagents

Table 1B. Reactions of α, β-Unsaturated Ketones with Heteroarylboron Reagents

Table 1C. Reactions of α, β-Unsaturated Ketones with Alkenylboron Reagents

Table 2A. Reactions of α, β-Unsaturated Aldehydes with Arylboron Reagents

Table 2C. Reactions of α, β-Unsaturated Aldehydes with Alkenylboron Reagents

Table 3A. Reactions of α, β-Unsaturated Esters with Arylboron Reagents

Table 3B. Reactions of α, β-Unsaturated Esters with Heteroarylboron Reagents

Table 3C. Reactions of α, β-Unsaturated Esters with Alkenylboron Reagents

Table 4A. Reactions of α, β-Unsaturated Amides with Arylboron Reagents

Table 4B. Reactions of α, β-Unsaturated Amides with Heteroarylboron Reagents

Table 4C. Reactions of α, β-Unsaturated Amides with Alkenylboron Reagents

Table 5A. Reactions of Alkenylphosphoryl Compounds with Arylboron Reagents

Table 6A. Reactions of Nitroalkenes with Arylboron Reagents

Table 6C. Reactions of Nitroalkenes with Alkenylboron Reagents

Table 7A. Reactions of Alkenylsulfonyl Compounds with Arylboron Reagents

Table 7C. Reactions of Alkenylsulfonyl Compounds with Alkenylboron Reagents

Table 8A. Reactions of Alkenylazaarenes with Arylboron Reagents

Table 8C. Reactions of Alkenylazaarenes with Alkenylboron Reagents

Table 9A. Reactions of Electron-Deficient Alkenylarenes with Arylboron Reagents

Table 10A. Reactions of Borylalkenes with Arylboron Reagents

Table 11A. Reactions of Miscellaneous Acceptors with Arylboron Reagents

Table 12A. Domino Reactions with Arylboron Reagents

Table 12B. Domino Reactions with Heteroarylboron Reagents

Table 12D. Domino Reactions with Alkylboron Reagents

Advisory Board

John E. Baldwin

Peter Beak

Dale L. Boger

André B. Charette

Engelbert Ciganek

Dennis Curran

Samuel Danishefsky

Huw M. L. Davies

John Fried

Jacquelyn Gervay-Hague

Heinz W. Gschwend

Stephen Hanessian

Louis Hegedus

Paul J. Hergenrother

Robert C. Kelly

Andrew S. Kende

Laura Kiessling

Steven V. Ley

James A. Marshall

Michael J. Martinelli

Stuart W. McCombie

Jerrold Meinwald

Scott J. Miller

Larry E. Overman

Leo A. Paquette

Gary H. Posner

T. V. RajanBabu

Hans J. Reich

James H. Rigby

William R. Roush

Scott D. Rychnovsky

Martin Semmelhack

Charles Sih

Amos B. Smith, III

Barry M. Trost

James D. White

Peter Wipf

Former Members of the Board Now Deceased

Roger Adams

Homer Adkins

Werner E. Bachmann

A. H. Blatt

Robert Bittman

Virgil Boekelheide

George A. Boswell, Jr.

Theodore L. Cairns

Arthur C. Cope

Donald J. Cram

David Y. Curtin

William G. Dauben

Richard F. Heck

Louis F. Fieser

Ralph F. Hirshmann

Herbert O. House

John R. Johnson

Robert M. Joyce

Willy Leimgruber

Frank C. McGrew

Blaine C. McKusick

Carl Niemann

Harold R. Snyder

Mil'an Uskokovic

Boris Weinstein

Organic Reactions

Volume 93

Editorial Board

Scott E. Denmark, Editor-in-Chief

Jeffrey Aubé

David B. Berkowitz

David B. Berkowitz

Carl Busacca

Jin K. Cha

P. Andrew Evans

Paul L. Feldman

Dennis G. Hall

Donna M. Huryn

Marisa C. Kozlowski

Gary A. Molander

John Montgomery

Albert Padwa

Tomislav Rovis

Steven M. Weinreb

Robert M. Coates, Secretary University of Illinois at Urbana-Champaign, Urbana, Illinois

Jeffery B. Press, Secretary Press Consulting Partners, Brewster, New York

Danielle Soenen, Editorial Coordinator

Landy K. Blasdel, Editorial Assistant

Dena Lindsay, Editorial Assistant

Linda S. Press, Editorial Consultant

Engelbert Ciganek, Editorial Advisor

Associate Editors

Alan R. Burns

Hon Wai Lam

Iain D. Roy

Iain D. Roy

Acknowledgments: The authors thank Daniel Best, David J. Burns, and Benjamin M. Partridge for assistance in the preparation of the Tables.

Copyright © 2017 by Organic Reactions, Inc. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey

Published simultaneously in Canada

No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, [phone], fax [phone], or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, [phone], fax [phone], or online at http://www.wiley.com/go/permission.

Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.

For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at [phone], outside the United States at [phone] or fax [phone].

Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com.

Library of Congress Cataloging-in-Publication Data:

ISBN: 978-1-119-28141-2

Introduction to the Series Roger Adams, 1942

In the course of nearly every program of research in organic chemistry, the investigator finds it necessary to use several of the better-known synthetic reactions. To discover the optimum conditions for the application of even the most familiar one to a compound not previously subjected to the reaction often requires an extensive search of the literature; even then a series of experiments may be necessary. When the results of the investigation are published, the synthesis, which may have required months of work, is usually described without comment. The background of knowledge and experience gained in the literature search and experimentation is thus lost to those who subsequently have occasion to apply the general method. The student of preparative organic chemistry faces similar difficulties. The textbooks and laboratory manuals furnish numerous examples of the application of various syntheses, but only rarely do they convey an accurate conception of the scope and usefulness of the processes.

For many years American organic chemists have discussed these problems. The plan of compiling critical discussions of the more important reactions thus was evolved. The volumes of Organic Reactions are collections of chapters each devoted to a single reaction, or a definite phase of a reaction, of wide applicability. The authors have had experience with the processes surveyed. The subjects are presented from the preparative viewpoint, and particular attention is given to limitations, interfering influences, effects of structure, and the selection of experimental techniques. Each chapter includes several detailed procedures illustrating the significant modifications of the method. Most of these procedures have been found satisfactory by the author or one of the editors, but unlike those in Organic Syntheses, they have not been subjected to careful testing in two or more laboratories. Each chapter contains tables that include all the examples of the reaction under consideration that the author has been able to find. It is inevitable, however, that in the search of the literature some examples will be missed, especially when the reaction is used as one step in an extended synthesis. Nevertheless, the investigator will be able to use the tables and their accompanying bibliographies in place of most or all of the literature search so often required. Because of the systematic arrangement of the material in the chapters and the entries in the tables, users of the books will be able to find information desired by reference to the table of contents of the appropriate chapter. In the interest of economy, the entries in the indices have been kept to a minimum, and, in particular, the compounds listed in the tables are not repeated in the indices.

The success of this publication, which will appear periodically, depends upon the cooperation of organic chemists and their willingness to devote time and effort to the preparation of the chapters. They have manifested their interest already by the almost unanimous acceptance of invitations to contribute to the work. The editors will welcome their continued interest and their suggestions for improvements in Organic Reactions.

Introduction to the Series Scott E. Denmark, 2008

In the intervening years since “The Chief” wrote this introduction to the second of his publishing creations, much in the world of chemistry has changed. In particular, the last decade has witnessed a revolution in the generation, dissemination, and availability of the chemical literature with the advent of electronic publication and abstracting services. Although the exponential growth in the chemical literature was one of the motivations for the creation of Organic Reactions, Adams could never have anticipated the impact of electronic access to the literature. Yet, as often happens with visionary advances, the value of this critical resource is now even greater than at its inception.

From 1942 to the 1980's the challenge that Organic Reactions successfully addressed was the difficulty in compiling an authoritative summary of a preparatively useful organic reaction from the primary literature. Practitioners interested in executing such a reaction (or simply learning about the features, advantages, and limitations of this process) would have a valuable resource to guide their experimentation. As abstracting services, in particular Chemical Abstracts and later Beilstein, entered the electronic age, the challenge for the practitioner was no longer to locate all of the literature on the subject. However, Organic Reactions chapters are much more than a surfeit of primary references; they constitute a distillation of this avalanche of information into the knowledge needed to correctly implement a reaction. It is in this capacity, namely to provide focused, scholarly, and comprehensive overviews of a given transformation, that Organic Reactions takes on even greater significance for the practice of chemical experimentation in the 21st century.

Adams' description of the content of the intended chapters is still remarkably relevant today. The development of new chemical reactions over the past decades has greatly accelerated and has embraced more sophisticated reagents derived from elements representing all reaches of the Periodic Table. Accordingly, the successful implementation of these transformations requires more stringent adherence to important experimental details and conditions. The suitability of a given reaction for an unknown application is best judged from the informed vantage point provided by precedent and guidelines offered by a knowledgeable author.

As Adams clearly understood, the ultimate success of the enterprise depends on the willingness of organic chemists to devote their time and efforts to the preparation of chapters. The fact that, at the dawn of the 21st century, the series continues to thrive is fitting testimony to those chemists whose contributions serve as the foundation of this edifice. Chemists who are considering the preparation of a manuscript for submission to Organic Reactions are urged to contact the Editor-in-Chief.

Preface to Volume 93

Boron has all the best tunes

A. J. Downs in

“Chemistry of Aluminum, Gallium, Indium and Thallium”

It is ironic that a book dedicated to the chemistry of the heavier elements in Group 13 would bemoan the dominance of the lightest, boron. The reality is, however, that for applications in synthetic chemistry, boron is unparalleled in its versatility to facilitate the formation of new carbon-carbon and carbon-heteroatom bonds in myriad structural settings with extraordinary generality and selectivity.

Undoubtedly, the ease with which boron engages in so many diverse chemical transformations can be ascribed to its unique ability to exist in both tricoordinate and tetracoordinate constitutions and to interconvert between them with relative ease. As a consequence, boron can function as a Lewis acidic species (6 electron, neutral) and a Lewis basic species (8 electron, anionic), which enables both electrophilic and nucleophilic character to be expressed. No other element has such chemical virtuosity and the manifestations of its unique behavior continue to be developed. As a testimony to the remarkable and enduring impact of organoboron chemistry, it is worth noting that the 1979 Nobel Prize in Chemistry was shared by Herbert C. Brown and Georg Wittig “