Chiral Allylsilane Additions to Chiral a-Substituted Aldehydes

Abstract

Chiral allylsilane 3 reacted with chiral alpha-methyl-beta-siloxy-aldehydes to afford the corresponding 1,4-syn-products with good diastereoselectivities independent of the absolute stereochemistry of these aldehydes. The best selectivities are observed when the reactions are carried out by transmetallation of the allylsilane 3 using Tin (IV) Chloride in CH2Cl2, at -78 °C, before addition of the aldehydes.

Keywords

• chiral allylsilane
• transmetallation
• 1,4-asymmetric induction
• polyacetate derived natural products