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Synlett 1992; 1992(8): 653-654
DOI: 10.1055/s-1992-21445
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Catalyzed Asymmetric SE′ Addition of Allylstannanes to Aldehydes

James A. Marshall* , Ying Tang
  • *Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, South Carolina 29208, USA
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Publication Date:
08 March 2002 (online)

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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.