Organic Reactions, Volume 93

By Wiley

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.

• Language: English
• Publisher: Wiley
• Release date: Aug 4, 2017
• ISBN: 9781119307136

Book preview

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

List of Illustrations

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

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

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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

Wiley Logo

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

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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