Highly diastereoselective aminobromination of β-methyl-β- nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources

Sheng Chen; Jianlin Han; Guigen Li; Yi Pan

doi:10.1016/j.tetlet.2013.02.113

Highly diastereoselective aminobromination of β-methyl-β- nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources

Sheng Chen, Jianlin Han, Guigen Li, Yi Pan

Chemistry and Biochemistry

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

3 Scopus citations

Abstract

A facile and stereoselective aminobromination reaction of α,β-unsaturated nitro compounds with t-butyl N,N-dibromocarbamate/t- butyl carbamate as bromine/nitrogen sources was reported. This catalytic system could tolerate a wide scope of β-methyl-β-nitrostyrenes, resulting in good chemical yields and excellent regio- and stereoselectivities. Furthermore, the N-t-butoxycarbonyl protecting group could be easily cleaved to afford the free vicinal haloamines.

Original language	English
Pages (from-to)	2781-2784
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2013.02.113
State	Published - May 29 2013

Keywords

Keywords Aminobromination β-Methyl-β-nitrostyrenes t-Butyl N,N-dibromocarbamate Bromoamines Deprotection

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@article{29166382d1b942669cc9b1e24719a45d,

title = "Highly diastereoselective aminobromination of β-methyl-β- nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources",

abstract = "A facile and stereoselective aminobromination reaction of α,β-unsaturated nitro compounds with t-butyl N,N-dibromocarbamate/t- butyl carbamate as bromine/nitrogen sources was reported. This catalytic system could tolerate a wide scope of β-methyl-β-nitrostyrenes, resulting in good chemical yields and excellent regio- and stereoselectivities. Furthermore, the N-t-butoxycarbonyl protecting group could be easily cleaved to afford the free vicinal haloamines.",

keywords = "Keywords Aminobromination β-Methyl-β-nitrostyrenes t-Butyl N,N-dibromocarbamate Bromoamines Deprotection",

author = "Sheng Chen and Jianlin Han and Guigen Li and Yi Pan",

note = "Funding Information: We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21102071 ) and the Fundamental Research Funds for the Central Universities (Nos. 1107020522 and 1082020502 ). The Jiangsu 333 program (for Pan) and Changzhou Jin-Feng-Huang program (for Han) are also acknowledged. ",

year = "2013",

month = may,

day = "29",

doi = "10.1016/j.tetlet.2013.02.113",

language = "English",

volume = "54",

pages = "2781--2784",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "22",

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TY - JOUR

T1 - Highly diastereoselective aminobromination of β-methyl-β- nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources

AU - Chen, Sheng

AU - Han, Jianlin

AU - Li, Guigen

AU - Pan, Yi

N1 - Funding Information: We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21102071 ) and the Fundamental Research Funds for the Central Universities (Nos. 1107020522 and 1082020502 ). The Jiangsu 333 program (for Pan) and Changzhou Jin-Feng-Huang program (for Han) are also acknowledged.

PY - 2013/5/29

Y1 - 2013/5/29

N2 - A facile and stereoselective aminobromination reaction of α,β-unsaturated nitro compounds with t-butyl N,N-dibromocarbamate/t- butyl carbamate as bromine/nitrogen sources was reported. This catalytic system could tolerate a wide scope of β-methyl-β-nitrostyrenes, resulting in good chemical yields and excellent regio- and stereoselectivities. Furthermore, the N-t-butoxycarbonyl protecting group could be easily cleaved to afford the free vicinal haloamines.

AB - A facile and stereoselective aminobromination reaction of α,β-unsaturated nitro compounds with t-butyl N,N-dibromocarbamate/t- butyl carbamate as bromine/nitrogen sources was reported. This catalytic system could tolerate a wide scope of β-methyl-β-nitrostyrenes, resulting in good chemical yields and excellent regio- and stereoselectivities. Furthermore, the N-t-butoxycarbonyl protecting group could be easily cleaved to afford the free vicinal haloamines.

KW - Keywords Aminobromination β-Methyl-β-nitrostyrenes t-Butyl N,N-dibromocarbamate Bromoamines Deprotection

UR - http://www.scopus.com/inward/record.url?scp=84876737616&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.02.113

DO - 10.1016/j.tetlet.2013.02.113

M3 - Article

AN - SCOPUS:84876737616

VL - 54

SP - 2781

EP - 2784

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 22

ER -

Highly diastereoselective aminobromination of β-methyl-β- nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources

Abstract

Keywords

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