A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1,3-oxathiolanes and vice versa employing organic ammonium tribromide (OATB)

被引:80
作者
Mondal, E
Sahu, PR
Bode, G
Khan, AT [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, Guwahati, India
[2] Visva Bharati Univ, Dept Chem, Shanti Niketan 731235, W Bengal, India
关键词
protection; deprotection; 1,3-oxathiolanes; n-tetrabutylammonium; tribromide (TBATB); cetyltrimethylammonium tribromide (CetTMATB);
D O I
10.1016/S0040-4039(02)00345-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A wide variety of carbonyl Compounds I can be easily protected selectively as the corresponding 1.3-oxathiolanes 2 in good yields using a catalytic amount (0.01-0.1 equiv.) of n-tetrabutylammonium tribromide in dry CH2Cl2 at 0-5 degreesC. On the other hand, various 1,3-oxathiolanes 2 can be deprotected chemoselectively to the parent carbonyl compounds I employing 0.5 equivalents of organic ammionum tribromides under identical conditions in verb high yields. Mild conditions, high selectivity and yield, highly efficient. less expensive, and no brominations either at the double bond or allylic position and even alpha- to the keto position or aromatic ring are some of the major advantages of the protocol. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2843 / 2846
页数:4
相关论文
共 32 条
[1]  
Barua PMB, 2002, SYNLETT, P81
[2]   An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n-tetrabutylammonium tribromide [J].
Bose, G ;
Mondal, E ;
Khan, AT ;
Bordoloi, MJ .
TETRAHEDRON LETTERS, 2001, 42 (50) :8907-8909
[3]   A convenient and useful method of preparation of α-bromo enones from the corresponding enones using organic ammonium tribromide (OATB) [J].
Bose, G ;
Barua, PMB ;
Chaudhuri, MK ;
Kalita, D ;
Khan, AT .
CHEMISTRY LETTERS, 2001, (04) :290-291
[4]   An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB) [J].
Chaudhuri, MK ;
Khan, AT ;
Patel, BK ;
Dey, D ;
Kharmawophlang, W ;
Lakshmiprabha, TR ;
Mandal, GC .
TETRAHEDRON LETTERS, 1998, 39 (44) :8163-8166
[5]  
Chavan SP, 2001, SYNLETT, P1251
[6]  
Clark J. H., 1995, CHEM WASTE MINIMIZAT
[7]   STUDIES IN ORGANIC SULFUR COMPOUNDS .6. CYCLIC ETHYLENE AND TRIMETHYLENE HEMITHIOKETALS [J].
DJERASSI, C ;
GORMAN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3704-3708
[8]   HIGHLY STEREOSELECTIVE ASYMMETRIC-SYNTHESIS OF (R)-(-)-MEVALOLACTONE [J].
ELIEL, EL ;
SOAI, K .
TETRAHEDRON LETTERS, 1981, 22 (30) :2859-2862
[9]   ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .1. SCOPE OF THE REACTION [J].
ELIEL, EL ;
MORRISNATSCHKE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2937-2942
[10]  
EMERSON DW, 1971, TETRAHEDRON LETT, P3445