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

Access to Document

10.1016/j.tetlet.2006.05.067

Cite this

@article{1c321b97f5b143efbdfcf789ee8cf528,

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",

month = jul,

day = "17",

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

language = "English (US)",

volume = "47",

pages = "5131--5134",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "29",

}

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

UR - http://www.scopus.com/inward/record.url?scp=33744979311&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33744979311&partnerID=8YFLogxK

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

Access to Document

Other files and links

Fingerprint

Cite this