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

Takuya Kochi; Tony P Tang; Jonathan A Ellman

doi:10.1021/ja026292g

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

J Am Chem Soc. 2002 Jun 12;124(23):6518-9. doi: 10.1021/ja026292g.

Authors

Takuya Kochi¹, Tony P Tang, Jonathan A Ellman

Affiliation

¹ Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.

PMID: 12047156
DOI: 10.1021/ja026292g

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amino Alcohols / chemical synthesis*
Stereoisomerism

Substances

Amino Alcohols