α-phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids

Chakrabortya, T. K. ; Hussaina, K. Azhar ; Reddya, G. Venkat (1995) α-phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids Tetrahedron, 51 (33). pp. 9179-9190. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4020(95)00523-B

Abstract

The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative cleavage make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular mechanics calculations are carried out to explain the observed diastereoselection.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:69594
Deposited On:14 Nov 2011 03:50
Last Modified:14 Nov 2011 03:50

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