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Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones.

Abstract:
5-Aryl-1,3-dioxolan-4-one heterocycles derived from mandelic acid derivatives and hexafluoroacetone have been identified as new and effective pro-nucleophiles in highly diastereo- and enantioselective Michael addition reactions to nitro olefins catalyzed by bifunctional epi-9-amino-9-deoxy cinchona alkaloid derivatives. Diastereoselectivities up to 98% and enantioselectivities up to 89% for a range of nitro olefins and 5-aryl-1,3-dioxolan-4-ones under mild reaction conditions are reported.
Publication status:
Published

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Publisher copy:
10.1021/ol070532l

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
9
Issue:
11
Pages:
2107-2110
Publication date:
2007-05-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:baa67c4e-a1cf-477a-8ff9-34361cbc57e1
Source identifiers:
40308
Local pid:
pubs:40308
Language:
English

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