Synlett 2002(2): 0247-0250
DOI: 10.1055/s-2002-19746
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct Conversion of Esters to Hydroxyamides on Solid Support - a Key Step en route to Bisoxazoline Ligands

Avi Weissberg, Moshe Portnoy*
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Ramat Aviv, Tel Aviv 69978, Israel
Fax: +972(3)6409293; e-Mail: portnoy@post.tau.ac.il;
Further Information

Publication History

Received 26 November 2001
Publication Date:
02 February 2007 (online)

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Abstract

A method for converting esters into β-hydroxyamides via their direct reaction with β-aminoalcohols was implemented for the first time on solid support. The transformation is performed under basic conditions and presumably includes transesterification followed by rapid intramolecular O,N-acyl transfer. The technique was successfully tested on monoesters as well as malonates. The transformation of malonates is a key step in the on-resin assembly of bisoxazoline ligands, demonstrated here for the first time.