CaltechAUTHORS
Published October 28, 2005 | Version public
Journal Article Metadata-only

Deracemization of Quaternary Stereocenters by Pd-Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β-Ketoesters

Creators

  • 1. ROR icon California Institute of Technology

Abstract

Stereochemical alchemy! Racemic allyl β-ketoesters allow the regiocontrolled formation of enolates, where the same catalyst is intimately involved in both the stereoablative (C-C bond-breaking) and stereoselective (C-C bond-forming) steps. This mechanistic and practical insight led to the formation of multiple quaternary carbon stereocenters in a single cascade reaction (see scheme).

Additional Information

© 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: June 11, 2005; Published online: October 5, 2005. The authors wish to thank the Fannie and John Hertz Foundation (predoctoral fellowship to D.C.B.), the NIH (postdoctoral fellowship to A.M.H.), Research Corporation, the Camille and Henry Dreyfus Foundation, Merck, Pfizer, and Lilly for financial support, and Prof. D. A. Dougherty for helpful discussions.

Additional details

Identifiers

Eprint ID
74345
DOI
10.1002/anie.200502018
Resolver ID
CaltechAUTHORS:20170215-153759053

Funding

Fannie and John Hertz Foundation
NIH Postdoctoral Fellowship
Research Corporation
Camille and Henry Dreyfus Foundation
Merck
Pfizer
Eli Lilly

Dates

Created
2017-02-16
Created from EPrint's datestamp field
Updated
2021-11-11
Created from EPrint's last_modified field