Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes |
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| Authors: | Guz Nathan R Phillips Andrew J |
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| Affiliation: | Department of Chemistry and Biochemistry, University of Colorado at Boulder, Boulder, Colorado 80309-0215, USA. |
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| Abstract: | [reaction: see text] The 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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