Diastereoselective Synthesis of anti-1,2-Diols from α-Silyloxyaldehydes

Significance

Allylic 1,2-diols are interesting and useful intermediates, for instance, in the synthesis of complex natural products. This reaction offers an elegant and attractive method for the diastereo­selective preparation of anti-1,2-diols with an allylic double bond starting from readily available chiral α-silyloxyaldehydes. Very good regioselectivity together with high diastereoselectivity is observed for this process. Various internal alkynes undergo this reaction, giving rise to a variety of available products. The use of silylalkynes followed by the protodesilylation allows the preparation of allylic alcohols with disubstituted double bonds.