Synthesis 2015; 47(23): 3776-3782
DOI: 10.1055/s-0035-1560088
paper
© Georg Thieme Verlag Stuttgart · New York

Racemization-Free Synthesis of Morpholinone Derivatives from α-Amino Acids

Sauvik Samanta
Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India   Email: [email protected]
,
Abhijit Mal
Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India   Email: [email protected]
,
Sandipan Halder
Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India   Email: [email protected]
,
Manas K. Ghorai*
Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India   Email: [email protected]
› Author Affiliations
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

 
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  • 19 The ee of morpholinone 2b (>99%), as a representative example of morpholinones 2af, was determined by chiral HPLC analysis.
  • 20 See the Supporting Information for details.
  • 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: [email protected]; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
  • 22 The ee of morpholine 9a (>99%), as a representative example of morpholines 9a and 9b, was determined by chiral HPLC analysis.
  • 23 The ee of morpholine 11a (>99%), as a representative example of morpholines 11ad, was determined by chiral HPLC analysis.