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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 12
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Original Articles

A Simple and Direct Synthesis of Erythro‐β‐amino‐α‐hydroxy Esters from trans‐β‐Phenylglycidic Ester

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Pages 2185-2194 | Received 18 Aug 2003, Published online: 17 Aug 2006
 

Abstract

trans‐β‐Phenylglycidic esters undergo ring opening when treated in tert‐butyl alcohol with primary amines (R–NH2, with R = secondary group or tertiary group), which attacks epoxide exclusively at C‐3 and avoids aminolysis of the ester group affording the erythro‐β‐amino‐α‐hydroxy esters as the sole product.

Acknowledgment

We thank Pr. Driss A. for providing the x‐ray crystal analysis. Thanks are also due to Pr. Labassi T. for interesting and valuable English discussions.

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