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

来源：

CHEMISTRY LETTERS | 2006年 / 35卷 / 04期

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

页码：358 / 359

页数：2

共 50 条

[31] Synthesis of 2,4,5-trisubstituted pyrimidines from Baylis-Hillman adducts and amidines
Department of Chemistry, Institute of Basic Science, Chonnam National University, Gwangju 500-757, Korea, Republic of
Bull. Korean Chem. Soc., 2007, 12 (2505-2507):
[32] Facile synthesis of aza-Baylis-Hillman adducts of cycloalkenones:: FeCl3-mediated direct Amination of Baylis-Hillman alcohols
Lee, Ka Young
Lee, Hyun Seung
Kim, Jae Nyoung
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (06): : 1099 - 1100
[33] Applications of the Baylis-Hillman adducts in organic synthesis:: A facile synthesis of [E]-α-cyanocinnamyl alcohols and [E]-α-cyanocinnamic aldehydes
Basavaiah, D
Kumaragurubaran, N
Padmaja, K
SYNLETT, 1999, (10) : 1630 - 1632
[34] An efficient and stereoselective synthesis of (Z)-allyl chlorides from Baylis-Hillman adducts using Vilsmeier-Haack reagent
Liu, Y.
Zheng, H.
Xu, D.
Xu, Z.
Zhang, Y.
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2007, 39 (02) : 190 - 195
[35] Synthetic applications of Baylis-Hillman chemistry:: An efficient and solely stereoselective synthesis of (E)-α-methylcinnamic acids and potent hypolipidemic agent LK-903 from unmodified Baylis-Hillman adducts
Das, Biswanath
Banerjee, Joydeep
Chowdhury, Nikhil
Majhi, Anjoy
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (12) : 1725 - 1727
[36] A Pd(OAc)2-mediated one-pot synthesis of trisubstituted alkenes via Michael addition of a stabilized ylide to baylis-hillman adducts
Murthy, A. Sai Krishna
Rambabu, C.
Vijeender, K.
Bhusan, P. Bibhuti
Chandrasekhar, S.
SYNLETT, 2007, (03) : 494 - 496
[37] A Rapid and Efficient Synthesis of Allyl Iodides from Baylis-Hillman Adducts: A Facile Synthesis of Semiplenamide D
Das, Biswanath
Srinivas, Yallamalla
Sudhakar, Chithaluri
Damodar, Kongara
Reddy, Parigi Raghavendar
CHEMISTRY LETTERS, 2010, 39 (03) : 246 - 247
[38] Synthesis of stereochemically defined (E)-cinnamyl alcohol derivatives from the Baylis-Hillman adducts
Kim, HS
Kim, TY
Lee, KY
Chung, YM
Lee, HJ
Kim, JN
TETRAHEDRON LETTERS, 2000, 41 (15) : 2613 - 2616
[39] BAYLIS-HILLMAN REACTION - MAGNESIUM BROMIDE AS A STEREOSELECTIVE REAGENT FOR THE SYNTHESIS OF [E]-ALLYL AND [Z]-ALLYL BROMIDES
BASAVAIAH, D
BHAVANI, AKD
PANDIARAJU, S
SARMA, PKS
SYNLETT, 1995, (03) : 243 - 244
[40] Electrochemical Stereoselective Synthesis of (Z)-Allyl Aryl Selenides and Sulfides from Baylis-Hillman Acetates
Sun, Li
Xia, Mengcan
Yu, Guorui
Liu, Sheng
Wu, Yafei
Zhao, Kun
Mao, Biming
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (05) : 1152 - 1157

← 1 2 3 4 5 →