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

被引：54

作者：

Li, GG ^{[1
]}

Kim, SH ^{[1
]}

Wei, HX ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 45期

关键词：

diamination; vicinal diamines; nitrobenzenesulfonamide; alpha; beta-diamino acids;

D O I：

10.1016/S0040-4039(00)01579-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem diamination of cinnamic esters provides a new approach to anti alkyl N alpha-(2-Ns), N beta -Ac diaminophenylpropionates. The new reaction proceeds to completion within 3 hours at room temperature using N,N-dichloro-2-nitrobenzenesulfonamide (2-NsNCl(2)) 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. All rights reserved.

引用

页码：8699 / 8703

页数：5

共 18 条

[1] BAUDOUX D, 1984, B SOC CHIM BELG, V93, P1009
[2] Scale up of a Ritter reaction
Chang, SJ
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (03) : 232 - 234
[3] SYNTHESIS OF DIOXOBIS(TERT-ALKYLIMIDO)OSMIUM(VIII) AND OXOTRIS(TERT-ALKYLIMIDO)OSMIUM(VIII) COMPLEXES - STEREOSPECIFIC VICINAL DIAMINATION OF OLEFINS
CHONG, AO
OSHIMA, K
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) : 3420 - 3426
[4] Two expedient methods for the preparation of chiral diamines
de Sousa, SE
O'Brien, P
Poumellec, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09): : 1483 - 1492
[5] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
EVANS, DA
FAUL, MM
BILODEAU, MT
ANDERSON, BA
BARNES, DM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5328 - 5329
[6] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES
FUKUYAMA, T
JOW, CK
CHEUNG, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (36) : 6373 - 6374
[7] Erythro-selective aldol-type reaction of N-sulfonylaldimines with methyl isocyanoacetate catalyzed by gold(I)
Hayashi, T
Kishi, E
Soloshonok, VA
Uozumi, Y
[J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4969 - 4972
[8] HELMCHEN G, 1996, HOUBENWEYL, V9, P5295
[9] Krimen L. I., 1969, ORG REACT, V17, P213, DOI DOI 10.1002/0471264180.0R017.03
[10] Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters
Li, GG
Wei, HX
Kim, SH
Neighbors, M
[J]. ORGANIC LETTERS, 1999, 1 (03) : 395 - 397

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