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An organocatalytic asymmetric chlorolactonization.

ABSTRACT: A reagent controlled organocatalytic enantioselective chlorolactonization reaction has been developed. Several 4-aryl pentenoic acids were cyclized in the presence of 0.1 equiv of (DHQD)(2)PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source. Ten examples are presented with selectivities ranging from 43 to 90% ee. This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantioselectivities.

SUBMITTER: Whitehead DC

PROVIDER: S-EPMC2883568 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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An organocatalytic asymmetric chlorolactonization.

Whitehead Daniel C DC Yousefi Roozbeh R Jaganathan Arvind A Borhan Babak B

Journal of the American Chemical Society 20100301 10

A reagent controlled organocatalytic enantioselective chlorolactonization reaction has been developed. Several 4-aryl pentenoic acids were cyclized in the presence of 0.1 equiv of (DHQD)(2)PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source. Ten examples are presented with selectivities ranging from 43 to 90% ee. This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantioselectivi ...[more]

PMID: 20170118

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