Synthesis of Enantiopure syn-β-Amino Alcohols. A Simple Case of Chelation-Controlled Additions of Diethylzinc to α-(Dibenzylamino) Aldehydes
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (13) , 4210-4213
- https://doi.org/10.1021/jo960017t
Abstract
Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral α-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76−98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.Keywords
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