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Letter

An Amino Alcohol Ligand for Highly Enantioselective Addition of Organozinc Reagents to Aldehydes: Serendipity Rules

Supporting Info

William A. Nugent

Bristol-Myers Squibb Company, Process Research and Development Department, Chambers Works, P.O. Box 269, Deepwater, New Jersey 08023-0269

Org. Lett., 2002, 4 (13), pp 2133–2136

DOI: 10.1021/ol0259488

Publication Date (Web): May 25, 2002

william.nugent@bms.com

Abstract

Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.

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Published In Issue June 27, 2002
Received March 29, 2002

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Letter

An Amino Alcohol Ligand for Highly Enantioselective Addition of Organozinc Reagents to Aldehydes: Serendipity Rules