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Catalyzed Asymmetric SE′ Addition of Allylstannanes to Aldehydes
08 March 2002 (online)
Addition of achiral allylstannanes to achiral aldehydes in the presence of Yamamoto's chiral (acyloxy)borane catalyst (III) and trifluoroacetic anhydride affords homoallylic alcohols with high diastereo- and enantioselectivity. For example, crotonoaldehyde (1c) and (E)-tributyl(2-methyl-2-pentenyl)stannane (2) gave (3S,4S,5E)-3-ethyl-2-methyl-1,5-heptadien-4-ol (3c) in 85% yield and 95% enantiomeric excess.