Title : Highly stereoselective oxy-Michael additions to alpha,beta-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected alpha-hydroxy ketones.

Pub. Date : 2004 Oct 21

PMID : 15480457






1 Functional Relationships(s)
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1 The "naked" anion of (S)-6-methyl delta lactol undergoes efficient oxy-Michael addition to alpha,beta-disubstituted nitro olefins to give the THP* protected Henry products with excellent (95-->98% de) stereocontrol at the beta-position and moderate (up to 3 : 1) stereocontrol at the alpha-position in favour of the syn-diastereoisomer. pirarubicin synemin Homo sapiens