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Synthesis of ?-hydroxy-?-haloesters through super silyl ester directed syn-selective aldol reaction.

ABSTRACT: Super silyl haloesters including chloro- and bromoacetate were synthesized and utilized for aldol reactions to give syn-?-hydroxy-?-haloacetates in good yields with high diastereoselectivities. ?-Hydroxy-?-fluoroacetate was obtained by lithiation of super silyl bromofluoroacetate. Sequential Darzens reactions provided cis-glycidic esters in moderate yields.

SUBMITTER: Oda S

PROVIDER: S-EPMC3946542 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Oda Susumu S Yamamoto Hisashi H

Organic letters 20131108 23

Super silyl haloesters including chloro- and bromoacetate were synthesized and utilized for aldol reactions to 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. ...[more]

PMID: 24205937

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