A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst

Paul McDaid; Yonggang Chen; Li Deng

doi:10.1002/1521-3773(20020118)41:2<338::AID-ANIE338>3.0.CO;2-M

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A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst

Journal article

Peer reviewed

A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst

Paul McDaid, Yonggang Chen and Li Deng

Angewandte Chemie (International ed.), Vol.41(2), pp.338-340

01/18/2002

DOI: https://doi.org/10.1002/1521-3773(20020118)41:2<338::AID-ANIE338>3.0.CO;2-M

PMID: 12491425

Abstract

Cyclopentanes - chemistry

Sulfhydryl Compounds - chemistry

Catalysis

Stereoisomerism

The mechanism is not yet known but the modified biscinchona alkaloid shown here is an excellent catalyst for the general and highly enantioselective 1,4‐addition of thiols to cyclic enones. Selectivities ranging from 93 to >99 % ee were achieved for the addition of 2‐thionaphthol to six‐ to nine‐membered enones.

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Title: A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst
Creators: Paul McDaid - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA
Yonggang Chen
Li Deng
Publication Details: Angewandte Chemie (International ed.), Vol.41(2), pp.338-340
Publisher: Germany
Grant note: GM-61591 / NIGMS NIH HHS
Identifiers: 9923957803901921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst

Abstract

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