Published in

American Chemical Society, Organic Letters, 18(7), p. 3849-3851, 2005

DOI: 10.1021/ol0513544

Wiley-VCH Verlag, ChemInform, 1(37), 2006

DOI: 10.1002/chin.200601108

Links

Tools

Export citation

Search in Google Scholar

Dual Catalyst Control in the Enantioselective Intramolecular Morita−Baylis−Hillman Reaction

Journal article published in 2005 by Carrie E. Aroyan, Melissa M. Vasbinder, Scott J. Miller ORCID
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

Full text: Unavailable

Green circle
Preprint: archiving allowed
  • Must obtain written permission from Editor
  • Must not violate ACS ethical Guidelines
Upload
Orange circle
Postprint: archiving restricted
  • Must obtain written permission from Editor
  • Must not violate ACS ethical Guidelines
Upload
Red circle
Published version: archiving forbidden
Policy details
Data provided by SHERPA/RoMEO

Abstract

The intramolecular Morita-Baylis-Hillman (MBH) reaction has been achieved with unprecedented levels of enantioselectivity. Using a co-catalyst system involving pipecolinic acid and N-methylimidazole, cyclic MBH products have been obtained with enantiomer ratios of 92:8 (84% ee). In addition, reactions may be carried out with a "kinetic resolution quench" involving acetic anhydride and an asymmetric acylation catalyst such that ee enhancement occurs to deliver products with >98% ee with an isolated yield of 50%. [reaction: see text]