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Synthesis 2015; 47(23): 3776-3782
DOI: 10.1055/s-0035-1560088
DOI: 10.1055/s-0035-1560088
paper
Racemization-Free Synthesis of Morpholinone Derivatives from α-Amino Acids
Further Information
Publication History
Received: 12 May 2015
Accepted after revision: 11 July 2015
Publication Date:
25 August 2015 (online)
Abstract
A simple strategy is reported for the synthesis of chiral N-protected morpholinone derivatives by a base (potassium carbonate)-mediated cyclization reaction of N-protected α-amino acids with 1,2-dibromoethane. The morpholinone derivatives are obtained in good yields and in enantiomerically pure forms.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560088.
- Supporting Information
-
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- 19 The ee of morpholinone 2b (>99%), as a representative example of morpholinones 2a–f, was determined by chiral HPLC analysis.
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- 21 Crystallographic data for compounds 2a and 2b have been deposited with the accession numbers CCDC 1033183 and 1033184, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
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- 23 The ee of morpholine 11a (>99%), as a representative example of morpholines 11a–d, was determined by chiral HPLC analysis.