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Enantioselective synthesis of tertiary ?-chloro esters by non-covalent catalysis.

ABSTRACT: We report an enantioselective approach to tertiary ?-chloro esters through the reaction of silyl ketene acetals and N-chlorosuccinimide. The reaction is promoted by a chiral squaramide catalyst, which is proposed to engage both reagents exclusively through non-covalent interactions. Application of the tertiary chloride products in stereospecific substitution reactions is demonstrated.

SUBMITTER: Liu RY

PROVIDER: S-EPMC4465138 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis.

Liu Richard Y RY Wasa Masayuki M Jacobsen Eric N EN

Tetrahedron letters 20150601 23

We report an enantioselective approach to tertiary α-chloro esters through the reaction of silyl ketene acetals and <i>N</i>-chlorosuccinimide. The reaction is promoted by a chiral squaramide catalyst, which is proposed to engage both reagents exclusively through non-covalent interactions. Application of the tertiary chloride products in stereospecific substitution reactions is demonstrated. ...[more]

PMID: 26085694

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