A facile Zn-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from Baylis-Hillman adducts in water and its application

被引:20
|
作者
Das, Biswanath [1 ]
Chowdhury, Nikhil [1 ]
Banerjee, Joydeep [1 ]
Majhi, Anjoy [1 ]
Mahender, Gurram [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1246/cl.2006.358
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH4Cl solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica (F).
引用
收藏
页码:358 / 359
页数:2
相关论文
共 50 条
  • [1] Stereoselective synthesis of trisubstituted alkenes containing (Z)-allylthio units from the acetates of Baylis-Hillman adducts
    Liu, Yunkui
    Xu, Danqian
    Xu, Zhenyuan
    Zhang, Yongmin
    HETEROATOM CHEMISTRY, 2008, 19 (02) : 188 - 198
  • [2] APPLICATIONS OF THE BAYLIS-HILLMAN REACTION-2 - A SIMPLE STEREOSELECTIVE SYNTHESIS OF (E)-TRISUBSTITUTED AND (Z)-TRISUBSTITUTED ALKENES
    BASAVAIAH, D
    SARMA, PKS
    BHAVANI, AKD
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (09) : 1091 - 1092
  • [3] Facile stereoselective synthesis of (E)- and (Z)-allyl bromides from the Baylis-Hillman adducts using MgBr2
    Ravichandran, S
    SYNTHETIC COMMUNICATIONS, 2001, 31 (13) : 2059 - 2062
  • [4] A highly efficient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts
    Das, B
    Majhi, A
    Banerjee, J
    Chowdhury, N
    Venkateswarlu, K
    TETRAHEDRON LETTERS, 2005, 46 (46) : 7913 - 7915
  • [5] A facile synthesis of [E]-α-cyanocinnamic aldehydes from Baylis-Hillman adducts
    Ravichandran, S
    SYNTHETIC COMMUNICATIONS, 2001, 31 (14) : 2185 - 2188
  • [6] FeCl3 and Yb(OTf)3 mediated conversion of acetates of the Baylis-Hillman adducts into (Z) and (E) trisubstituted alkenes
    Krishna, PR
    Kannan, V
    Sharma, GVM
    SYNTHETIC COMMUNICATIONS, 2004, 34 (01) : 55 - 64
  • [7] Chemo-, regio- and stereoselective addition of triorganoindium reagents to acetates of Baylis-Hillman adducts:: a new strategy for the synthesis of (E)- and (Z)-trisubstituted alkenes
    Ranu, Brindaban C.
    Chattopadhyay, Kalicharan
    Jana, Ranjan
    TETRAHEDRON LETTERS, 2007, 48 (22) : 3847 - 3850
  • [8] A facile synthesis of pyrazolines from Baylis-Hillman adducts
    Yadav, J. S.
    Singh, A. P.
    Bhunia, D. C.
    Basak, A. K.
    Srihari, P.
    CHEMISTRY LETTERS, 2008, 37 (06) : 624 - 625
  • [9] Montmorillonite K10 clay-microwave assisted isomerisation of acetates of the Baylis-Hillman adducts:: A facile method of stereoselective synthesis of (E)-trisubstituted alkenes
    Shanmugam, P
    Singh, PR
    SYNLETT, 2001, (08) : 1314 - 1316
  • [10] Trisubstituted alkene synthesis using the Baylis-Hillman adducts: Stereoselective synthesis of (E)- and (Z)-tertiary allyl amines and (E)-allyl nitrates.
    Rachakonda, SH
    Basavaiah, D
    Reddy, RM
    Kumaragurubaran, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U170 - U170