Enhanced diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes obtained from nerol and geraniol

Article abstract of DOI:10.1016/0040-4020(96)00453-X

Optically active α,β-epoxyaldehydes obtained from nerol and geraniol were allowed to react with lithium tert-butylacetate. The diastereofacial preference of the aldolisation reaction was always anti ('Si' face attack of the carbonyl). The best diastereoselectivity ever observed in these series (>99: <1 anti:syn) was obtained for the α,β-epoxyneral aldolisation.