An organocatalytic synthesis of N-sulfonyl imines using chloramine-T in aqueous medium

被引：14

作者：

Chawla, Ruchi ^{[1
]}

Singh, Atul K. ^{[1
]}

Yadav, Lal Dhar S. ^{[1
]}

机构：

[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 25期

关键词：

Aldehydes; Chloramine-T; N-Sulfonyl imines; Aqueous medium; Organocatalysis; DIELS-ALDER REACTIONS; CONJUGATE ADDITION; EFFICIENT; REAGENTS; ACID; 1-AZA-1,3-BUTADIENES; TOSYLIMINES; ALDIMINES; CATALYSIS; CHLORIDE;

D O I：

10.1016/j.tetlet.2014.04.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Sulfonyl imines have been synthesized in good to excellent yields from aldehydes and chloramine-T using proline as an organocatalyst in aqueous medium at ambient temperature. The protocol is applicable to a wide range of aldehydes, especially enals exhibit remarkable efficiency in the reaction. The reaction presumably occurs via iminium activation and opens new avenues for the synthesis of N-sulfonyl imines under environmentally benign and mild conditions. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3553 / 3556

页数：4

共 59 条

[1] Electrophilicities of Benzaldehyde-Derived Iminium Ions: Quantification of the Electrophilic Activation of Aldehydes by Iminium Formation
Appel, Roland
Chelli, Saloua
Tokuyasu, Takahiro
Troshin, Konstantin
Mayr, Herbert
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (17) : 6579 - 6587
[2] Asymmetric [4+2] cycloaddition of cyclopentadiene to N'-tosylimine of N-glyoxyloyl-(2R)-bornane-10,2-sultam
Bauer, T
Szymanski, S
Jezewski, A
Gluzinski, P
Jurczak, J
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2619 - 2625
[3] Dynamic imine chemistry
Belowich, Matthew E.
Stoddart, J. Fraser
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (06) : 2003 - 2024
[4] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
Bloch, R
[J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
[5] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF N-SULFONYL ALPHA,BETA-UNSATURATED IMINES - A GENERAL-APPROACH TO IMPLEMENTATION OF THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS
BOGER, DL
CORBETT, WL
CURRAN, TT
KASPER, AM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) : 1713 - 1729
[6] DIELS-ALDER REACTIONS OF 1-AZA-1,3-BUTADIENES - ROOM-TEMPERATURE, ENDO-SELECTIVE LUMODIENE-CONTROLLED [4+2]-CYCLOADDITION REACTIONS OF N-SULFONYL-4-(ETHOXYCARBONYL)-1-AZA-1,3-BUTADIENES
BOGER, DL
CURRAN, TT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) : 5439 - 5442
[7] K2S2O8-Mediated Aerobic Oxysulfonylation of Olefins into β-Keto Sulfones in Aqueous Media
Chawla, Ruchi
Singh, Atul K.
Yadav, Lal Dhar S.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) : 2032 - 2036
[8] Highly regioselective ring-opening of aziridines with arenesulfinates on water: a facile access to β-amino/vinyl sulfones
Chawla, Ruchi
Singh, Atul K.
Yadav, Lal Dhar S.
[J]. TETRAHEDRON, 2013, 69 (06) : 1720 - 1724
[9] Organocatalyzed stereoselective construction of N-formylpiperidines via a Michael-aza-Henry-hemiaminalization reaction cascade
Chawla, Ruchi
Rai, Ankita
Singh, Atul K.
Yadav, Lal Dhar S.
[J]. TETRAHEDRON LETTERS, 2012, 53 (39) : 5323 - 5326
[10] An organocatalyzed highly regioselective one-pot approach to the synthesis of tetrahydrobenzofuranones
Chawla, Ruchi
Singh, Atul K.
Yadav, Lal Dhar S.
[J]. TETRAHEDRON LETTERS, 2012, 53 (26) : 3382 - 3384

← 1 2 3 4 5 6 →