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

Peter S. Hynes; Daniela Stranges; Paul A. Stupple; Antonio Guarna; Darren J. Dixon

doi:10.1021/ol070532l

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

Peter S. Hynes, Daniela Stranges, Paul A. Stupple, Antonio Guarna, Darren J. Dixon

Research output: Contribution to journal › Article › Research › peer-review

79 Citations (Scopus)

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-amino9-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.

Original language	English
Pages (from-to)	2107-2110
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	11
DOIs	https://doi.org/10.1021/ol070532l
Publication status	Published - 24 May 2007
Externally published	Yes

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title = "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-amino9-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.",

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T1 - Organocatalytic diastereo- And enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones

AU - Hynes, Peter S.

AU - Stranges, Daniela

AU - Stupple, Paul A.

AU - Guarna, Antonio

AU - Dixon, Darren J.

PY - 2007/5/24

Y1 - 2007/5/24

N2 - 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-amino9-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.

AB - 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-amino9-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.

UR - http://www.scopus.com/inward/record.url?scp=34250626847&partnerID=8YFLogxK

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AN - SCOPUS:34250626847

SN - 1523-7060

VL - 9

SP - 2107

EP - 2110

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

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

Abstract

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