Synthesis 2015; 47(23): 3669-3672
DOI: 10.1055/s-0035-1560487
psp
© Georg Thieme Verlag Stuttgart · New York

A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates

Sudeshna Roy
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: cspill@umsl.edu
,
Nongnuch Sutivisedsak
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: cspill@umsl.edu
,
Bruce C. Hamper
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: cspill@umsl.edu
,
Alexander M. Lyss
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: cspill@umsl.edu
,
Christopher D. Spilling*
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: cspill@umsl.edu
› Author Affiliations
Further Information

Publication History

Received: 04 August 2015

Accepted after revision: 11 September 2015

Publication Date:
21 October 2015 (eFirst)

Abstract

The preparation of (S)- and (R)-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution.

Supporting Information

 
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