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Synthesis of β-Hydroxy-α-haloesters through Super Silyl Ester Directed Syn-Selective Aldol Reaction

Susumu Oda and Hisashi Yamamoto*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States, Email: yamamotouchicago.edu

S. Oda, H. Yamamoto, Org. Lett., 2013, 15, 6030-6033.

DOI: 10.1021/ol402928p (free Supporting Information)


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Abstract

Aldol reactions of super silyl haloesters including chloro- and bromoacetate give syn-β-hydroxy-α-haloacetates in good yields with high diastereoselectivities. β-Hydroxy-α-fluoroacetate was obtained by lithiation of super silyl bromofluoroacetate. Sequential Darzens reactions provided cis-glycidic esters in moderate yields.

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Key Words

aldol addition, α-chlorocarboxylic acids


ID: J54-Y2013