An Organocatalyzed enantioselective synthesis of (2S,3R,4S)-4-hydroxyisoleucine and its stereoisomers

Gullapalli Kumaraswamy; Neerasa Jayaprakash; Balasubramanian Sridhar

doi:10.1021/jo100233u

An Organocatalyzed enantioselective synthesis of (2S,3R,4S)-4-hydroxyisoleucine and its stereoisomers

J Org Chem. 2010 Apr 16;75(8):2745-7. doi: 10.1021/jo100233u.

Authors

Gullapalli Kumaraswamy¹, Neerasa Jayaprakash, Balasubramanian Sridhar

Affiliation

¹ Organic Division-III, Indian Institute of Chemical Technology, Hyderabad, 500 007, India. gkswamy_iict@yahoo.co.in

PMID: 20307090
DOI: 10.1021/jo100233u

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Isoleucine / analogs & derivatives*
Isoleucine / chemical synthesis
Isoleucine / chemistry
Kinetics
Stereoisomerism
Substrate Specificity

Substances

Isoleucine
(2S,3S,4R)-gamma-hydroxyisoleucine