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Synthesis 2009(8): 1403-1404  
DOI: 10.1055/s-0028-1088015
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© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of (R)-Propylene Carbonate from Ethyl (S)-Lactate

John M. Whitaker, Robert C. Ronald*
Department of Chemistry, Washington State University, Pullman, WA 99164, USA
Fax: +1(509)3358867; e-Mail: rcr@wsu.edu;
Further Information

Publication History

Received 17 October 2008
Publication Date:
16 March 2009 (online)

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Abstract

We report a three-step synthesis of (R)-propylene carbonate from inexpensive, chiral ethyl (S)-lactate. The synthesis involves a borohydride ester reduction and an unusual intramolecular displacement reaction by a carbonate anion. The procedure is simple and reliable, resulting in (R)-propylene carbonate in approximately 60% overall yield with ≥98% ee.

Key words

propylene carbonate - cyclic carbonate formation - borohydride reductions - nucleophilic addition - chiral pool

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