Remarkable increase in the diastereofacial selectivity of the addition of β-methyl α-(alkoxy)allylstannane to aldehydes: Substituent effects on diastereofacial selectivity

DOI: 10.1016/S0040-4039(00)71205-6

Source and publish data:

Tetrahedron Letters p. 13 - 16 (1991)

Update date:2022-07-30

Topics:

Authors:

Gung, Benjamin W.

Smith, Daniel T.

Wolf, Mark A.

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Article abstract of DOI:10.1016/S0040-4039(00)71205-6

Several new chiral allylstannanes were prepared and reacted with aldehydes. Excellent diastereofacial selectivity was observed for the reactions of allylstannane 1 with aldehydes in the presence of BF₃·Et₂O. This is in contrast to the results from other allylstannanes which do not bear a β-methyl group. These observations were rationalized based on a combination of steric and electronic effects.

Full text of DOI:10.1016/S0040-4039(00)71205-6

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