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

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.