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Cation-directed enantioselective synthesis of quaternary-substituted indolenines

Abstract:

An asymmetric method for the synthesis of quaternary-substituted indolenines via a 5-endo-dig cyclization of an α-cyanocarbanion onto an isonitrile has been developed. This transformation relies on Brønsted acid activation of the isonitrile functional group under asymmetric phase transfer conditions in the presence of a Brønsted base. Good to excellent levels of enantioselectivity were obtained (85:15 to 96:4 e.r., 18 examples) using a bespoke bifunctional catalyst. Enantioenriched indolenine...

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Publication status:
Published

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Publisher copy:
10.1039/c3sc50592h

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
CHEMICAL SCIENCE
Volume:
4
Issue:
7
Pages:
2907-2911
Publication date:
2013
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
URN:
uuid:6277be2d-f0a3-4f38-acda-b3ef7d1d218d
Source identifiers:
405821
Local pid:
pubs:405821
Language:
English

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