α,β-Differentiated tandem diamination of cinnamic esters using N,N-dichloro-2-nitrobenzenesulfonamide and acetonitrile as the nitrogen sources

G. Li; S. H. Kim; H. X. Wei

doi:10.1016/S0040-4039(00)01579-3

α,β-Differentiated tandem diamination of cinnamic esters using N,N-dichloro-2-nitrobenzenesulfonamide and acetonitrile as the nitrogen sources

G. Li, S. H. Kim, H. X. Wei

Chemistry and Biochemistry

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

54 Scopus citations

Abstract

Tandem diamination of cinnamic esters provides a new approach to anti alkyl Nα-(2-Ns), Nβ-Ac diaminophenylpropionates. The new reaction proceeds to completion within 3 hours at room temperature using N,N-dichloro-2-nitrobenzenesulfonamide (2-NsNCl₂) as the nitrogen source in acetonitrile, which is also involved in the reaction process. Seven diamine derivatives have been obtained with good yields and stereoselectivity. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	8699-8703
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(00)01579-3
State	Published - Nov 4 2000

Keywords

Diamination
Nitrobenzenesulfonamide
Vicinal diamines
α,β-diamino acids

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10.1016/S0040-4039(00)01579-3

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title = "α,β-Differentiated tandem diamination of cinnamic esters using N,N-dichloro-2-nitrobenzenesulfonamide and acetonitrile as the nitrogen sources",

abstract = "Tandem diamination of cinnamic esters provides a new approach to anti alkyl Nα-(2-Ns), Nβ-Ac diaminophenylpropionates. The new reaction proceeds to completion within 3 hours at room temperature using N,N-dichloro-2-nitrobenzenesulfonamide (2-NsNCl2) as the nitrogen source in acetonitrile, which is also involved in the reaction process. Seven diamine derivatives have been obtained with good yields and stereoselectivity. (C) 2000 Elsevier Science Ltd.",

keywords = "Diamination, Nitrobenzenesulfonamide, Vicinal diamines, α,β-diamino acids",

author = "G. Li and Kim, {S. H.} and Wei, {H. X.}",

note = "Funding Information: We would like to acknowledge the Robert A. Welch Foundation and the South Plains Foundation for supporting this work. We thank Mr. David W. Purkiss and Mr. Subramanian Karur for their assistance.",

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T1 - α,β-Differentiated tandem diamination of cinnamic esters using N,N-dichloro-2-nitrobenzenesulfonamide and acetonitrile as the nitrogen sources

AU - Li, G.

AU - Kim, S. H.

AU - Wei, H. X.

N1 - Funding Information: We would like to acknowledge the Robert A. Welch Foundation and the South Plains Foundation for supporting this work. We thank Mr. David W. Purkiss and Mr. Subramanian Karur for their assistance.

PY - 2000/11/4

Y1 - 2000/11/4

N2 - Tandem diamination of cinnamic esters provides a new approach to anti alkyl Nα-(2-Ns), Nβ-Ac diaminophenylpropionates. The new reaction proceeds to completion within 3 hours at room temperature using N,N-dichloro-2-nitrobenzenesulfonamide (2-NsNCl2) as the nitrogen source in acetonitrile, which is also involved in the reaction process. Seven diamine derivatives have been obtained with good yields and stereoselectivity. (C) 2000 Elsevier Science Ltd.

AB - Tandem diamination of cinnamic esters provides a new approach to anti alkyl Nα-(2-Ns), Nβ-Ac diaminophenylpropionates. The new reaction proceeds to completion within 3 hours at room temperature using N,N-dichloro-2-nitrobenzenesulfonamide (2-NsNCl2) as the nitrogen source in acetonitrile, which is also involved in the reaction process. Seven diamine derivatives have been obtained with good yields and stereoselectivity. (C) 2000 Elsevier Science Ltd.

KW - Diamination

KW - Nitrobenzenesulfonamide

KW - Vicinal diamines

KW - α,β-diamino acids

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U2 - 10.1016/S0040-4039(00)01579-3

DO - 10.1016/S0040-4039(00)01579-3

M3 - Article

AN - SCOPUS:0034605847

SN - 0040-4039

VL - 41

SP - 8699

EP - 8703

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

α,β-Differentiated tandem diamination of cinnamic esters using N,N-dichloro-2-nitrobenzenesulfonamide and acetonitrile as the nitrogen sources

Abstract

Keywords

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