Asymmetric synthesis of syn- and anti-1,3-amino alcohols.

J Am Chem Soc

Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.

Published: June 2002

The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. Reduction of the beta-hydroxy-N-sulfinyl imine products with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohol derivatives, respectively, with very high diastereomeric ratios.

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http://dx.doi.org/10.1021/ja026292gDOI Listing

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