Chemistry Letters, Vol.34, No.10, 1432-1433, 2005
Stereoselective construction of 1,3-diol derivatives via nucleophilic reaction to beta-methoxyacylsilanes
The stereoselectivity of 1,3-asymmetric induction in the nucleophilic addition to beta-methoxyacylsilanes having no substituent at the alpha-position is largely dependent on the kind of nucleophiles. In a similar reaction employed a-substituted beta-methoxyacylsilanes, three diastereoisomers of 1,3-diol derivatives having the three contiguous stereogenic centers among four possible diastereomeric products are yielded with high stereoselectivity. The protiodesilylation of the resulting alpha-silylalcohols proceeds with complete retention of the configuration.