Chemische Berichte

Chiral Vinyl Anions for “Carbonyl Umpolung”. Highly Stereoselective Addition of a Novel Enantiomerically Pure Vinyllithium Reagent to Aldehydes

H Mahler, M Braun

Index: Mahler, Hellmut; Braun, Manfred Chemische Berichte, 1991 ,  vol. 124,  # 6  p. 1379 - 1395

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Citation Number: 29

Abstract

The vinyllithium reagent 13 and its enantiomer are generated by a bromine/lithium exchange reaction starting from dibromoalkenes 11 and 12, both available from the corresponding enantiomer of alkyl lactate. When 13 is allowed to react with aldehydes or with acetophenone, a highly stereoselective addition to the Re face of the carbonyl compounds occurs to give predominantly the diastereomers 15. Alkenes 25a, c, ...