An efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from unactivated Baylis-Hillman adducts using NaBH4/CuCl2•2H2O

被引:31
作者
Das, B [1 ]
Banerjee, J [1 ]
Majhi, A [1 ]
Mahender, G [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India
关键词
unactivated Baylis-Hillman adduct; (Z)- and (E)-trisubstituted alkenes; NaBH4/CuCl center dot 2H(2)O; metallic halides; stereochemistry;
D O I
10.1016/j.tetlet.2004.10.088
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and facile stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been achieved by treatment of unactivated Baylis-Hillman adducts with NaBH4 in the presence of CuCl(2)(.)2H(2)O at room temperature for 15 min. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9225 / 9227
页数:3
相关论文
共 18 条
[1]   NUCLEOPHILIC-SUBSTITUTION OF FUNCTIONAL ALLYLIC CYCLOALKENOL ACETATES BY ORGANOMETAL COMPOUNDS IN THE PRESENCE OF COPPER-SALTS - APPLICATION TO RAPID SYNTHESIS OF MITSUGASHIWALACTONE [J].
AMRI, H ;
RAMBAUD, M ;
VILLIERAS, J .
TETRAHEDRON, 1990, 46 (10) :3535-3546
[2]   A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids [J].
Basavaiah, D ;
Krishnamacharyulu, M ;
Hyma, RS ;
Sarma, PKS ;
Kumaragurubaran, N .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1197-1200
[3]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[4]  
Baylis A. B, 1972, German Patent, Patent No. 2155113
[5]   MULTICOMPONENT ALARM PHEROMONES OF WEAVER ANT [J].
BRADSHAW, JWS ;
BAKER, R ;
HOWSE, PE .
NATURE, 1975, 258 (5532) :230-231
[6]   GENERAL STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED ALKENES VIA STEPWISE HYDROBORATION [J].
BROWN, HC ;
BASAVAIAH, D .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5407-5409
[7]   A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides [J].
Das, B ;
Banerjee, J ;
Ravindranath, N .
TETRAHEDRON, 2004, 60 (38) :8357-8361
[8]   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
[9]   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
[10]   A NEW, GENERAL, AND STEREOSELECTIVE METHOD FOR THE SYNTHESIS OF TRISUBSTITUTED ALKENES [J].
DENMARK, SE ;
AMBURGEY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10386-10387