Practical and Highly Selective Oxazolidinethione-Based Asymmetric Acetate Aldol Reactions with Aliphatic Aldehydes
2002; American Chemical Society; Volume: 4; Issue: 13 Linguagem: Inglês
10.1021/ol026108w
ISSN1523-7060
AutoresNathan R. Guz, Andrew J. Phillips,
Tópico(s)Chemical Synthesis and Reactions
ResumoThe utility of a valine-derived oxazolidinethione for auxiliary-based asymmetric acetate aldol reactions is reported. Titanium(IV) chloride, along with (−)-sparteine and N-methylpyrrolidinone, is employed for enolization. Subsequent aldol reaction with aliphatic aldehydes occurs with high diastereoselectivity (from 92:8 to 99:1 dr).
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