Issue 26, 2012

Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones

Abstract

N-Phenylsulfonyl (S)-proline catalyzes the direct aldol reaction of 3-substituted cyclobutanones and aryl aldehydes in good yield and with excellent diastereoselectivity and enantioselectivity. This desymmetrization process provides highly functionalized cyclobutanones with control over three contiguous stereogenic centers.

Graphical abstract: Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones

Supplementary files

Article information

Article type
Paper
Submitted
27 Apr 2012
Accepted
03 May 2012
First published
03 May 2012

Org. Biomol. Chem., 2012,10, 5045-5048

Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones

D. J. Aitken, A. M. Bernard, F. Capitta, A. Frongia, R. Guillot, J. Ollivier, P. P. Piras, F. Secci and M. Spiga, Org. Biomol. Chem., 2012, 10, 5045 DOI: 10.1039/C2OB25813G

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