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Stereoselective syntheses of protected β-hydroxy-ct-amino acids using (arylthio)nitrooxiranes

Lookup NU author(s): Professor Richard Jackson

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Abstract

The scope and limitations of a method for the stereocontrolled synthesis of a range of protected β-hydroxy-a-amino acids have been established. The method comprises condensation of a chiral, enantiomerically pure aldehyde 6 with (4-methylphenylthio)nitromethane 7 to form a 1-arylthio-l-nitroalkene 8; stereoselective epoxidation of this alkene with a metal alkyl peroxide; and stereospecific reaction of the arylthionitrooxirane with a nitrogen nucleophile to give an ci-amino thioester. This method has been employed in the synthesis of protected derivatives of both diastereoisomers of threonine 1 and 2, and of β-hydroxyleucine 3 and 4 and a synthesis of the a/!//-diasterebisomer of β-phenylserine 5.

Publication metadata

Author(s): Adams ZM, Jackson RFW, Palmer NJ, Rami HK, Jwythes M

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society - Perkin Transactions 1

Year: 1999

Issue: 8

Pages: 937-947

Print publication date: 01/01/1999

ISSN (print): 0300-922X

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/a901077g

DOI: 10.1039/a901077g

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