A domino copper-catalyzed C-O coupling-Claisen rearrangement process

Gero Nordmann; Stephen L Buchwald

doi:10.1021/ja034809y

A domino copper-catalyzed C-O coupling-Claisen rearrangement process

J Am Chem Soc. 2003 Apr 30;125(17):4978-9. doi: 10.1021/ja034809y.

Authors

Gero Nordmann¹, Stephen L Buchwald

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

PMID: 12708838
DOI: 10.1021/ja034809y

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Allyl Compounds / chemical synthesis*
Catalysis
Copper / chemistry*
Ethers / chemical synthesis*
Stereoisomerism
Vinyl Compounds / chemical synthesis*

Substances

Allyl Compounds
Ethers
Vinyl Compounds
Copper

Grants and funding

GM 45906/GM/NIGMS NIH HHS/United States