Abstract

This article describes the attractive method for construction of acyclic systems using diastereoselective addition reactions of nucleophiles with chiral carbonyl compounds. The following topics are included : (a) the diastereofacial selective addition reaction of α-alkyl-β-trimethylsilyl-β, γ-unsaturated carbonyl compounds with nucleophiles and its application to the synthesis of some natural products including macrolides, (b) the addition reaction of Grignard reagents with α-alkoxy-β-trimethylsilyl-β, γ-unsaturated carbonyl compounds which affords the convenient method for construction of 1, 2-diol derivatives, and (c) the synthesis of the rarely obtained syn-adducts in the reaction of organocopper compounds with glyceraldehyde acetonide.

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