An expedient stereoselective synthesis of (Z)- and (E)-ally iodides from Baylis-Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane-iodine system

被引:20
作者
Das, Biswanath [1 ]
Holla, Harish
Srinivas, Yallamalla
Chowdhury, Nikhil
Bandgar, B. P.
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
[2] Swami Ramanand Teerth Marathwada Univ, Sch Chem Sci, Organ Chem Res Lab, Vishnupuri 431606, Nanded, India
关键词
Baylis-Hillman adduct; (Z)- and (E)-Allyl iodides; polymethylhydrosiloxane (PMHS); iodine; benzylic iodide;
D O I
10.1016/j.tetlet.2007.03.050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective method has been developed for the synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. In addition, the reagent system has been utilized for the iodination of benzylic alcohols selectively. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3201 / 3204
页数:4
相关论文
共 27 条
[11]   Organic reactions in water:: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides [J].
Das, B ;
Banerjee, J ;
Mahender, G ;
Majhi, A .
ORGANIC LETTERS, 2004, 6 (19) :3349-3352
[12]   Convenient and efficient stereoselective synthesis of (2Z)-2(chloromethyl)alk-2-enoates using iron(III) or indium(III) chloride [J].
Das, B ;
Banerjee, J ;
Ravindranath, N ;
Venkataiah, B .
TETRAHEDRON LETTERS, 2004, 45 (11) :2425-2426
[13]   Efficient, selective deprotection of aromatic acetates catalyzed by Amberlyst-15 or iodine [J].
Das, B ;
Banerjee, J ;
Ramu, R ;
Pal, R ;
Ravindranath, N ;
Ramesh, C .
TETRAHEDRON LETTERS, 2003, 44 (29) :5465-5468
[14]   Studies on novel synthetic methodologies, part 85.: Iodine as an efficient catalyst for one-pot multicomponent synthesis of β-acetamido ketones [J].
Das, Biswanath ;
Reddy, K. Ravinder ;
Ramu, R. ;
Thirupathi, P. ;
Ravikanth, B. .
SYNLETT, 2006, (11) :1756-1758
[15]   Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes [J].
Das, Biswanath ;
Ravikanth, B. ;
Ramu, R. ;
Laxminarayana, K. ;
Rao, B. Vittal .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 255 (1-2) :74-77
[16]   SPECIFIC SYNTHESIS OF ETHYL (2Z)-2-BROMOMETHYL-2-BUTENOATE AND ITS CONVERSION INTO MIKANECIC ESTER [J].
GOLDBERG, O ;
DREIDING, AS .
HELVETICA CHIMICA ACTA, 1976, 59 (05) :1904-1910
[17]  
GRUIEC A, 1991, NEW J CHEM, V15, P943
[18]   DABCO-CATALYZED COUPLING OF ALDEHYDES WITH ACTIVATED DOUBLE-BONDS .1. PREPARATION OF 2-(1-HYDROXYALKYL)ACRYLIC ESTERS - SIMPLE 3-STEP SYNTHESIS OF MIKANECIC ACID [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10) :795-796
[20]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110