Highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid derived primary amine

Wenjing Liu; Desheng Mei; Wei Wang; Wenhu Duan

doi:10.1016/j.tetlet.2013.05.019

Highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid derived primary amine

Wenjing Liu
, Desheng Mei
, Wei Wang
, Wenhu Duan

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

19 Scopus citations

Abstract

A cinchona alkaloid derived primary amine catalyzed conjugate addition of nitroalkanes to enones is described. The process affords the Michael adducts in good yield and with up to 99% ee for both acyclic and cyclic enones.

Original language	English (US)
Pages (from-to)	3791-3793
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2013.05.019
State	Published - Jul 17 2013
Externally published	Yes

Keywords

Asymmetric conjugate addition
Chiral primary amine catalysis
Cinchona alkaloids
Enones
Nitroalkanes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.05.019

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title = "Highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid derived primary amine",

abstract = "A cinchona alkaloid derived primary amine catalyzed conjugate addition of nitroalkanes to enones is described. The process affords the Michael adducts in good yield and with up to 99\% ee for both acyclic and cyclic enones.",

keywords = "Asymmetric conjugate addition, Chiral primary amine catalysis, Cinchona alkaloids, Enones, Nitroalkanes",

author = "Wenjing Liu and Desheng Mei and Wei Wang and Wenhu Duan",

note = "Funding Information: Financial support of this research from the Chinese National Natural Science Foundation (Nos. 81102461 , 81021062 , and 90813034 ), the Chinese National Programs for High Technology Research and Development (No. 2012AA020302 ), and the NSF ( CHE-1057569 ) is gratefully acknowledged. ",

year = "2013",

month = jul,

day = "17",

doi = "10.1016/j.tetlet.2013.05.019",

language = "English (US)",

volume = "54",

pages = "3791--3793",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "29",

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TY - JOUR

T1 - Highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid derived primary amine

AU - Liu, Wenjing

AU - Mei, Desheng

AU - Wang, Wei

AU - Duan, Wenhu

N1 - Funding Information: Financial support of this research from the Chinese National Natural Science Foundation (Nos. 81102461 , 81021062 , and 90813034 ), the Chinese National Programs for High Technology Research and Development (No. 2012AA020302 ), and the NSF ( CHE-1057569 ) is gratefully acknowledged.

PY - 2013/7/17

Y1 - 2013/7/17

N2 - A cinchona alkaloid derived primary amine catalyzed conjugate addition of nitroalkanes to enones is described. The process affords the Michael adducts in good yield and with up to 99% ee for both acyclic and cyclic enones.

AB - A cinchona alkaloid derived primary amine catalyzed conjugate addition of nitroalkanes to enones is described. The process affords the Michael adducts in good yield and with up to 99% ee for both acyclic and cyclic enones.

KW - Asymmetric conjugate addition

KW - Chiral primary amine catalysis

KW - Cinchona alkaloids

KW - Enones

KW - Nitroalkanes

UR - https://www.scopus.com/pages/publications/84879020673

UR - https://www.scopus.com/pages/publications/84879020673#tab=citedBy

U2 - 10.1016/j.tetlet.2013.05.019

DO - 10.1016/j.tetlet.2013.05.019

M3 - Article

AN - SCOPUS:84879020673

SN - 0040-4039

VL - 54

SP - 3791

EP - 3793

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid derived primary amine

Abstract

Keywords

ASJC Scopus subject areas

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