α-Acetoxysulfones as "Chiral Aldehyde" Equivalents
Barry M. Trost*, Matthew L. Crawley and Chul Bom Lee
*Department of Chemistry, Stanford University Stanford, California 94305-5080
B. M. Trost, M. L. Crawley, C. B. Lee, J. Am. Chem. Soc., 2000, 122, 6120-6121.
DOI: 10.1021/ja000390p
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Abstract
Acetoxysulfones can serve as a novel class of chiral aldehyde equivalents that are acid-stable but base-labile. The two functionalities impart good diastereoselectivity in an electrophilic addition to the double bond. Thus, the availability of the acetoxysulfones in high enantiopurity translates to an asymmetric addition to one of the two enantiotopic faces of an α,β-unsaturated aldehyde.
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Key Words
ID: J48-Y2000
