Catalyzed Asymmetric SE′ Addition of Allylstannanes to Aldehydes

James A. Marshall; Ying Tang

doi:10.1055/s-1992-21445

Synlett 1992; 1992(8): 653-654
DOI: 10.1055/s-1992-21445

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Catalyzed Asymmetric S_E′ 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

Abstract

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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.

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