Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters

Guigen Li; Han Xun Wei; Sun Hee Kim; Margret Neighbors

doi:10.1021/ol990059e

Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters

Guigen Li, Han Xun Wei, Sun Hee Kim, Margret Neighbors

Chemistry and Biochemistry

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

103 Scopus citations

Abstract

(formula presented) A new aminohalogenation process has been developed for the synthesis of vicinal haloamine derivatives using cinnamic esters as substrates. The reaction was performed in CH₃CN using ZnCl₂ or Cu(OTf)₂ as catalyst and N,N-dichloro-p-toluenesulfonamide as chlorine/nitrogen source. Good to excellent yields and regio-and stereoselectivities have been obtained. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.

Original language	English
Pages (from-to)	395-397
Number of pages	3
Journal	Organic Letters
Volume	1
Issue number	3
DOIs	https://doi.org/10.1021/ol990059e
State	Published - Aug 12 1999

Access to Document

10.1021/ol990059e

Cite this

@article{ee60b1ad68da4135b0f2517cef8025f2,

title = "Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters",

abstract = "(formula presented) A new aminohalogenation process has been developed for the synthesis of vicinal haloamine derivatives using cinnamic esters as substrates. The reaction was performed in CH3CN using ZnCl2 or Cu(OTf)2 as catalyst and N,N-dichloro-p-toluenesulfonamide as chlorine/nitrogen source. Good to excellent yields and regio-and stereoselectivities have been obtained. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.",

author = "Guigen Li and Wei, {Han Xun} and Kim, {Sun Hee} and Margret Neighbors",

year = "1999",

month = aug,

day = "12",

doi = "10.1021/ol990059e",

language = "English",

volume = "1",

pages = "395--397",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "3",

}

TY - JOUR

T1 - Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters

AU - Li, Guigen

AU - Wei, Han Xun

AU - Kim, Sun Hee

AU - Neighbors, Margret

PY - 1999/8/12

Y1 - 1999/8/12

N2 - (formula presented) A new aminohalogenation process has been developed for the synthesis of vicinal haloamine derivatives using cinnamic esters as substrates. The reaction was performed in CH3CN using ZnCl2 or Cu(OTf)2 as catalyst and N,N-dichloro-p-toluenesulfonamide as chlorine/nitrogen source. Good to excellent yields and regio-and stereoselectivities have been obtained. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.

AB - (formula presented) A new aminohalogenation process has been developed for the synthesis of vicinal haloamine derivatives using cinnamic esters as substrates. The reaction was performed in CH3CN using ZnCl2 or Cu(OTf)2 as catalyst and N,N-dichloro-p-toluenesulfonamide as chlorine/nitrogen source. Good to excellent yields and regio-and stereoselectivities have been obtained. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.

UR - http://www.scopus.com/inward/record.url?scp=0001071513&partnerID=8YFLogxK

U2 - 10.1021/ol990059e

DO - 10.1021/ol990059e

M3 - Article

AN - SCOPUS:0001071513

SN - 1523-7060

VL - 1

SP - 395

EP - 397

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters

Abstract

Access to Document

Other files and links

Fingerprint

Cite this