Catalyst-free aza-Michael addition of azole to β,γ-unsaturated- α-keto ester: An efficient access to C-N bond formation

Jun WANG; Peng Fei Li; Sau Hing Chan; Albert S.C. Chan; Fuk Yee Kwong

doi:10.1016/j.tetlet.2012.03.132

Catalyst-free aza-Michael addition of azole to β,γ-unsaturated- α-keto ester: An efficient access to C-N bond formation

Jun WANG
, Peng Fei Li^*
, Sau Hing Chan
, Albert S.C. Chan
, Fuk Yee Kwong

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

38 Citations (Scopus)

Abstract

An efficient aza-Michael addition of azoles to β,γ-unsaturated- α-keto esters under room temperature conditions has been developed. In this conjugate addition, no additional catalyst is employed. Azole reacts with β,γ-unsaturated-α-keto ester smoothly to afford new C-N bond adducts in good to excellent yields (up to 96%).

Original language	English
Pages (from-to)	2887-2889
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2012.03.132
Publication status	Published - 6 Jun 2012

User-Defined Keywords

Amination
Azole
Michael addition
Nitroalkene
Nitroolefin

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10.1016/j.tetlet.2012.03.132

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@article{8392bc3c4c4145388645bb0759ed04b8,

title = "Catalyst-free aza-Michael addition of azole to β,γ-unsaturated- α-keto ester: An efficient access to C-N bond formation",

abstract = "An efficient aza-Michael addition of azoles to β,γ-unsaturated- α-keto esters under room temperature conditions has been developed. In this conjugate addition, no additional catalyst is employed. Azole reacts with β,γ-unsaturated-α-keto ester smoothly to afford new C-N bond adducts in good to excellent yields (up to 96\%).",

keywords = "Amination, Azole, Michael addition, Nitroalkene, Nitroolefin",

author = "Jun WANG and Li, \{Peng Fei\} and Chan, \{Sau Hing\} and Chan, \{Albert S.C.\} and Kwong, \{Fuk Yee\}",

note = "Funding Information: We thank the European Commission EP7 (CATAFLU.OR project), Research Grants Council of Hong Kong (GRF: PolyU 5010/11P), State Key Laboratory of Chirosciences (4-BBX3) and PolyU Internal Grant DA (A-PD0X) for financial support. Mr. Shun Man Wong and Ms. Pui Ying Choy (PolyU) are gratefully acknowledged for supporting the azole substrates. ",

year = "2012",

month = jun,

day = "6",

doi = "10.1016/j.tetlet.2012.03.132",

language = "English",

volume = "53",

pages = "2887--2889",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "23",

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TY - JOUR

T1 - Catalyst-free aza-Michael addition of azole to β,γ-unsaturated- α-keto ester

T2 - An efficient access to C-N bond formation

AU - WANG, Jun

AU - Li, Peng Fei

AU - Chan, Sau Hing

AU - Chan, Albert S.C.

AU - Kwong, Fuk Yee

N1 - Funding Information: We thank the European Commission EP7 (CATAFLU.OR project), Research Grants Council of Hong Kong (GRF: PolyU 5010/11P), State Key Laboratory of Chirosciences (4-BBX3) and PolyU Internal Grant DA (A-PD0X) for financial support. Mr. Shun Man Wong and Ms. Pui Ying Choy (PolyU) are gratefully acknowledged for supporting the azole substrates.

PY - 2012/6/6

Y1 - 2012/6/6

N2 - An efficient aza-Michael addition of azoles to β,γ-unsaturated- α-keto esters under room temperature conditions has been developed. In this conjugate addition, no additional catalyst is employed. Azole reacts with β,γ-unsaturated-α-keto ester smoothly to afford new C-N bond adducts in good to excellent yields (up to 96%).

AB - An efficient aza-Michael addition of azoles to β,γ-unsaturated- α-keto esters under room temperature conditions has been developed. In this conjugate addition, no additional catalyst is employed. Azole reacts with β,γ-unsaturated-α-keto ester smoothly to afford new C-N bond adducts in good to excellent yields (up to 96%).

KW - Amination

KW - Azole

KW - Michael addition

KW - Nitroalkene

KW - Nitroolefin

UR - https://www.scopus.com/pages/publications/84860836640

UR - http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000304387800023&KeyUID=WOS:000304387800023

U2 - 10.1016/j.tetlet.2012.03.132

DO - 10.1016/j.tetlet.2012.03.132

M3 - Journal article

AN - SCOPUS:84860836640

SN - 0040-4039

VL - 53

SP - 2887

EP - 2889

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Catalyst-free aza-Michael addition of azole to β,γ-unsaturated- α-keto ester: An efficient access to C-N bond formation

Abstract

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