Abstract (Z)‐(α‐Chlorocrotyl)boronates 3 add to nonchiral aldehydes to give homoallyl alcohols 5 with a syn‐β‐positioned methyl group and an (E)‐chloroalkenyl unit. The diastereoselectivity in favour of 5 is around 90%. The corresponding (E)‐(α‐chlorocrotyl)boronates 6 similarly lead to homoallyl alcohols 7 with an anti‐β‐methyl group and a (Z)‐chloroalkenyl unit, the diastereoselectivity being > 95%. Using optically active boronate 6 the resulting homoallyl alcohols 7 are obtained with > 95% e.e.
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Hoffmann et al. (1988) studied this question.
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