The use of certain types of atropisomeric amides, incorporating an N-MEM-ortho-tert-butylaniline group, for stereoselective reactions, has been explored. Enolate reactions of these systems are highly diastereocontrolled, and enantiomerically enriched starting materials can be obtained, starting from lactic acid, via a new SmI2 mediated reduction process.
A. D. Hughes, D. A. Price and N. S. Simpkins, J. Chem. Soc., Perkin Trans. 1, 1999, 1295 DOI: 10.1039/A901154D
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