Enantioselective allylation of β, γ-unsaturated aldehydes generated via Lewis Acid induced rearrangement of 2-vinyloxiranes

M Lautens, ML Maddess, ELO Sauer, SG Ouellet

Index: Lautens, Mark; Maddess, Matthew L.; Sauer, Effiette L. O.; Ouellet, Stephane G. Organic Letters, 2002 , vol. 4, # 1 p. 83 - 86

Full Text: HTML

Citation Number: 31

Abstract

2-Vinyloxiranes have been found to be excellent surrogates to β, γ-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc (OTf) 3, are effectively trapped by the chiral allylating agents based on α-pinene, affording bishomoallylic alcohols in high yield and excellent selectivity.