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Synlett 2005(4): 693-696  
DOI: 10.1055/s-2005-863740
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© Georg Thieme Verlag Stuttgart · New York

An Improved Synthesis of Optically Pure 4-Boc-5,6-Diphenylmorpholin-2-one and 4-Cbz-5,6-Diphenylmorpholin-2-one

Kim A. Dastlik, Uta Sundermeier, Deidre M. Johns, Yuyin Chen, Robert M. Williams*
Colorado State University, Department of Chemistry, Fort Collins, Colorado, 80523, USA
Fax: +1(970)4913944; e-Mail: rmw@lamar.colostate.edu;
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Publication History

Received 17 November 2004
Publication Date:
22 February 2005 (online)

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Abstract

A convenient synthesis of optically pure 4-Boc-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one by reaction of (+)- or (-)-2-amino-1,2-diphenylethanol with ethyl bromoacetate, followed by N-protection, and p-TsOH-mediated ring-closure is described. The title compounds can be used as synthons for the asymmetric synthesis of N-protected α-amino acids. These lactones are quite stable to storage and handling.

Key words

amino acids - asymmetric synthesis - lactones - 2-amino-1,2-diphenylethanol - ring-closure