Highly regioselective ring-opening of aziridines with arenesulfinates on water: a facile access to β-amino/vinyl sulfones

被引:25
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
关键词
Aziridines; Sodium sulfinates; beta-Amino sulfones; Vinyl sulfones; Green methodology; HIV PROTEASE INHIBITORS; AZA-MICHAEL ADDITION; ALPHA-AMINO-ACIDS; VINYL SULFONES; HYDROXY SULFONES; STEREOSELECTIVE-SYNTHESIS; PIPERIDINE-DERIVATIVES; ASYMMETRIC-SYNTHESIS; ANTHRANILIC ACIDS; ALKENYL SULFONES;
D O I
10.1016/j.tet.2012.12.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a LiBr catalyzed efficient synthesis of beta-amino sulfones from readily available aziridines and sodium sulfinates in good to excellent yields. The synthetic potential of beta-amino sulfones has also been demonstrated by their facile conversion to the corresponding vinyl sulfones. The use of water as reaction media, atom-economy and isolation of products by simple filtration in the case of solid beta-amino sulfones are certain green virtues of the synthetic protocol. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1720 / 1724
页数:5
相关论文
共 63 条
[1]   Lithiated beta-aminoalkyl sulfones as mono and dinucleophiles in the preparation of nitrogen heterocycles: Application to the synthesis of capsazepine [J].
Alonso, DA ;
Costa, A ;
Mancheno, B ;
Najera, C .
TETRAHEDRON, 1997, 53 (13) :4791-4814
[2]  
[Anonymous], SICHUAN MENTAL HLTH
[4]   Asymmetric synthesis of functionalized piperidine derivatives:: synthesis of (S)-anatabine [J].
Balasubramanian, T ;
Hassner, A .
TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2201-2205
[5]   Chemoselective O-methylation of phenols under non-aqueous condition [J].
Basak, A ;
Nayak, MK ;
Chakraborti, AK .
TETRAHEDRON LETTERS, 1998, 39 (27) :4883-4886
[6]   REGIOSELECTIVE RING-OPENING OF OXIRANES CATALYZED BY MONTMORILLONITE CLAY - A SIMPLE SYNTHESIS OF BETA-HYDROXY SULFONES [J].
BISWAS, GK ;
BHATTACHARYYA, P .
SYNTHETIC COMMUNICATIONS, 1991, 21 (04) :569-573
[7]   A stereoselective approach to polyhydroxylated quinolizidine alkaloids [J].
Carretero, JC ;
Arrayas, RG ;
deGracia, IS .
TETRAHEDRON LETTERS, 1997, 38 (49) :8537-8540
[8]  
Carretero JC, 1999, SYNLETT, P49
[9]   Stereoselective synthesis of polyhydroxylated indolizidines from γ-hydroxy α,β-unsaturated sulfones [J].
Carretero, JC ;
Arrayás, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2993-3005
[10]   Lithium bromide, an inexpensive and efficient catalyst for opening of epoxide rings by amines at room temperature under solvent-free condition [J].
Chakraborti, AK ;
Rudrawar, S ;
Kondaskar, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (17) :3597-3600