Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether

Liansuo Zu; Hao Li; Jian Wang; Xinhong Yu; Wei Wang

doi:10.1016/j.tetlet.2006.05.067

Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether

Liansuo Zu, Hao Li, Jian Wang, Xinhong Yu, Wei Wang

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

105 Scopus citations

Abstract

A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C₈F₁₇ fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process.

Original language	English (US)
Pages (from-to)	5131-5134
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.067
State	Published - Jul 17 2006
Externally published	Yes

Keywords

Asymmetric organocatalysis
Diphenylpyrrolinol silyl ether
Fluorous chemistry
Michael addition reaction
Nitroolefin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.05.067

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title = "Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether",

abstract = "A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C8F17 fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process.",

keywords = "Asymmetric organocatalysis, Diphenylpyrrolinol silyl ether, Fluorous chemistry, Michael addition reaction, Nitroolefin",

author = "Liansuo Zu and Hao Li and Jian Wang and Xinhong Yu and Wei Wang",

note = "Funding Information: The financial support by the Department of Chemistry and the Research Allocation Committee, University of New Mexico, NIH-INBRE (P20 RR016480) and kind gift from the American Chemical Society-PRF (G1 type) is gratefully acknowledged. ",

year = "2006",

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doi = "10.1016/j.tetlet.2006.05.067",

language = "English (US)",

volume = "47",

pages = "5131--5134",

journal = "Tetrahedron Letters",

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number = "29",

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TY - JOUR

T1 - Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether

AU - Zu, Liansuo

AU - Li, Hao

AU - Wang, Jian

AU - Yu, Xinhong

AU - Wang, Wei

N1 - Funding Information: The financial support by the Department of Chemistry and the Research Allocation Committee, University of New Mexico, NIH-INBRE (P20 RR016480) and kind gift from the American Chemical Society-PRF (G1 type) is gratefully acknowledged.

PY - 2006/7/17

Y1 - 2006/7/17

N2 - A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C8F17 fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process.

AB - A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C8F17 fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process.

KW - Asymmetric organocatalysis

KW - Diphenylpyrrolinol silyl ether

KW - Fluorous chemistry

KW - Michael addition reaction

KW - Nitroolefin

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U2 - 10.1016/j.tetlet.2006.05.067

DO - 10.1016/j.tetlet.2006.05.067

M3 - Article

AN - SCOPUS:33744979311

SN - 0040-4039

VL - 47

SP - 5131

EP - 5134

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether

Abstract

Keywords

ASJC Scopus subject areas

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