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Communication

A Domino Copper-Catalyzed C−O Coupling−Claisen Rearrangement Process

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Gero Nordmann and Stephen L. Buchwald*

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2003, 125 (17), pp 4978–4979

DOI: 10.1021/ja034809y

Publication Date (Web): April 4, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sbuchwal@mit.edu

Abstract

A practical method for the diastereoselective generation of two adjacent quarternary stereocenters by combining a copper-catalyzed C−O coupling reaction with a subsequent Claisen rearrangement in a one-pot domino process is described. Furthermore, an experimentally simple method for the stereoselective synthesis of a variety of different types of vinyl ethers is delineated using the same catalyst system.

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Published In Issue April 30, 2003
Received February 21, 2003

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Communication

A Domino Copper-Catalyzed C−O Coupling−Claisen Rearrangement Process

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

N- versus O-Arylation of Aminoalcohols: Orthogonal Selectivity in Copper-Based Catalysts

An Improved Cu-Based Catalyst System for the Reactions of Alcohols with Aryl Halides

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