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

Access to Document

10.1016/j.tetlet.2013.05.019

Cite this

@article{f26577392d1d4a2b920df954a65092b4,

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 Limited",

number = "29",

}

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 - http://www.scopus.com/inward/record.url?scp=84879020673&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84879020673&partnerID=8YFLogxK

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

Access to Document

Other files and links

Fingerprint

Cite this