S. Tanielyan, N. Marin, G. Alvez
Aug 11, 2006
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0
Influential Citations
15
Citations
Journal
Organic Process Research & Development
Abstract
Two enantioselective methods for the synthesis of 2-amino-1-phenylethanol have been developed. The first utilizes an enantioselective oxazaborolidine-catalyzed borane reduction of 2-chloroacetophenone (phenacyl chloride) to give the chiral chloro alcohol in good yield with an ee in the 93−97% range. Reaction with dilute ammonium hydroxide produced the amino alcohol in good yield with a high ee. The second approach involved first the conversion of phenacyl chloride to the succinimido acetophenone which was then hydrogenated using a chiral ruthenium complex in conjunction with a base and an optically active amine (Noyori procedure). This gave the optically active succinimido alcohol in very good yield with an ee of 98%. Hydrolysis with dilute base produced the optically active amino alcohol in very good yield and excellent enantioselectivity.