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Enantio- and diastereoselective catalytic alkylation reactions with aziridines.

Abstract:

The first asymmetric phase transfer catalyzed alkylation reaction of a range of carbon acids with N-sulfonyl aziridines is reported. When 10 mol % of a cinchona derived quaternary ammonium salt was employed as the catalyst under mildly basic conditions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amino ethylene products in consistently high yields and high enantioselectivities (up to 97% ee). By employing substituted aziridines in single enantiome...

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Publication status:
Published

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Publisher copy:
10.1021/ja8036965

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Journal of the American Chemical Society
Volume:
130
Issue:
31
Pages:
10076-10077
Publication date:
2008-08-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:3241e7b5-b1f9-414b-a4c4-2d2cf6388fb1
Source identifiers:
34305
Local pid:
pubs:34305

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