Tetrahedron: Asymmetry

Enantioselective synthesis of (S, S)-ethambutol using proline-catalyzed asymmetric α-aminooxylation and α-amination

SP Kotkar, A Sudalai

Index: Kotkar, Shriram P.; Sudalai, Arumugam Tetrahedron Asymmetry, 2006 , vol. 17, # 11 p. 1738 - 1742

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Citation Number: 31

Abstract

The literature methods for the synthesis of (S,S)-ethambutol involve resolution of racemic 2-amino-1-butanol, 1 and 4 palladium catalyzed regio- and stereoselective epoxide opening by pthalimide as the key step, 5 and a chiral pool approach by using l-methionine as a chiral material. 3b As a part of our research program aimed at developing stereocontrolled synthesis of bioactive molecules, 6 we report a highly efficient synthesis of (S,S)-ethambutol 1 using ...