Kinetic Resolution in the Reaction of (2R,3R)-2,3-Diacetoxy- and (2R,3R)-2,3-Dibenzoyloxy-succinic Anhydrides with Racemic Alcohols
- 1 January 1979
- journal article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 32 (1) , 65-70
- https://doi.org/10.1071/ch9790065
Abstract
The stereoselectivity in the reaction of various racemic alcohols with (2R,3R)-2,3-diacetoxy-and (2R,3R)-2,3-dibenzoyloxy-succinic anhydrides has been studied. Kinetic resolution values ranged up to 48%. A correlation between the absolute configuration of the more reactive enantiomeric alcohol with that of the chiral anhydride has been obtained. Attempted regeneration of the alcohols from the derived half-esters in the above reaction leads to partial racemization.Keywords
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