Highly regioselective ring opening of epoxides and aziridines using (bromodimethyl)sulfonium bromide

被引:59
作者
Das, Biswanath [1 ]
Krishnaiah, Maddeboina [1 ]
Venkateswarlu, Katta [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
epoxide; aziridine; (bromodimethyl)sulfonium bromide; regioselectivity;
D O I
10.1016/j.tetlet.2006.04.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Epoxides and aziridines undergo ring opening efficiently with (bromodimethyl)sulfonium bromide at room temperature to form the corresponding beta-bromohydrins and beta-bromoamines, respectively. The conversions are highly regioselective and afford the products in excellent yields within a short period of time. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4457 / 4460
页数:4
相关论文
共 19 条
[1]   A stereoselective synthesis of silylated polyunsaturated halides from α,β-epoxysilanes [J].
Babudri, F ;
Fiandanese, V ;
Marchese, G ;
Punzi, A .
TETRAHEDRON, 2001, 57 (03) :549-554
[2]   Easy access to β-halo amino esters and aziridine 2-carboxylic esters from halohydrins [J].
Boukhris, S ;
Souizi, A .
TETRAHEDRON LETTERS, 2003, 44 (16) :3259-3261
[3]   Studies on novel synthetic methodologies, part 62.: Fe3+-K-10 montmorillonite clay catalyzed friedel-crafts reaction of unactivated Baylis-Hillman adducts:: An efficient stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent [J].
Das, B ;
Majhi, A ;
Banerjee, J ;
Chowdhury, N ;
Venkateswarlu, K .
CHEMISTRY LETTERS, 2005, 34 (11) :1492-1493
[4]   Studies on novel synthetic methodologies, part 59.: A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst [J].
Das, B ;
Venkateswarlu, K ;
Mahender, G ;
Mahender, L .
TETRAHEDRON LETTERS, 2005, 46 (17) :3041-3044
[5]   Studies on novel synthetic methodologiess Part 39. Simple, mild and efficient thioacetalization and transthioacetalization of carbonyl compounds and deprotection of thioacetals: Unique role of thiols in the selectivity of thioacetalization [J].
Das, B ;
Ramu, R ;
Reddy, MR ;
Mahender, G .
SYNTHESIS-STUTTGART, 2005, (02) :250-254
[6]   A highly efficient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts [J].
Das, B ;
Majhi, A ;
Banerjee, J ;
Chowdhury, N ;
Venkateswarlu, K .
TETRAHEDRON LETTERS, 2005, 46 (46) :7913-7915
[7]  
FURUKAWA N, 1973, J CHEM SOC CHEM COMM, P212
[8]  
Kemp J. E. G., 1991, COMPREHENSIVE ORGANI, V7, P469, DOI DOI 10.1016/B978-0-08-052349-1.00199-2
[9]   A simple and practical synthetic protocol for acetalisation, thioacetalisation and transthioacetalisation of carbonyl compounds under solvent-free conditions [J].
Khan, AT ;
Mondal, E ;
Ghosh, S ;
Islam, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (09) :2002-2009
[10]  
Konnaklieva M. I., 1992, TETRAHEDRON LETT, V33, P7093