An Organocatalyzed Enantioselective Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers

A concise enantioselective total synthesis of (2S,3R,4S)-4-hydroxyisoleucine and its stereoisomers is described. A key feature of this protocol is a catalytic enantioselective mannich reaction that is either anti- or syn-selective as genesis of chirality.

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Bibliographic Details
Published in:Journal of organic chemistry 2010-04, Vol.75 (8), p.2745-2747
Main Authors: Kumaraswamy, Gullapalli, Jayaprakash, Neerasa, Sridhar, Balasubramanian
Format: Article
Language:English
Subjects:
Aliphatic compounds
Catalysis
Chemistry
Exact sciences and technology
Isoleucine - analogs & derivatives
Isoleucine - chemical synthesis
Isoleucine - chemistry
Kinetics
Organic chemistry
Preparations and properties
Stereoisomerism
Substrate Specificity
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Description
Summary:A concise enantioselective total synthesis of (2S,3R,4S)-4-hydroxyisoleucine and its stereoisomers is described. A key feature of this protocol is a catalytic enantioselective mannich reaction that is either anti- or syn-selective as genesis of chirality.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo100233u