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

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 alcoho...

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Bibliographic Details
Published in:Organic letters 2002-06, Vol.4 (13), p.2133-2136
Main Author: Nugent, William A
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Ligands
Morpholines - chemistry
Organometallic Compounds - chemistry
Stereoisomerism
Structure-Activity Relationship
Zinc - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0259488