Alkaloids-catalyzed regio- and enantioselective allylic nucleophilic substitution of tert-butyl carbonate of the Morita-Baylis-Hillman products

被引:122
作者
Du, YS [1 ]
Han, XL [1 ]
Lu, XY [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetlet.2004.04.135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alkaloids-catalyzed regio- and enantioselective allylic nucleophilic substitution reactions of tert-butyl carbonate of the Morita-Baylis-Hillman products with pronucleophiles are reported. A number of pronucleophiles, such as nitrogen, oxygen, and active carbon pronucleophiles have been used in this facile reaction. In general, the reaction proceeded efficiently to give the Substitution product in good yields with high regioselectivity and medium enantioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4967 / 4971
页数:5
相关论文
共 43 条
[1]   The use of enantiomerically pure N-sulfinimines in asymmetric Baylis-Hillman reactions [J].
Aggarwal, VK ;
Castro, AMM ;
Mereu, A ;
Adams, H .
TETRAHEDRON LETTERS, 2002, 43 (08) :1577-1581
[2]   Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications [J].
Aggarwal, VK ;
Mereu, A .
CHEMICAL COMMUNICATIONS, 1999, (22) :2311-2312
[3]   Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].
Aggarwal, VK ;
Mereu, A ;
Tarver, GJ ;
McCague, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189
[4]  
AYED TB, 2000, TETRAHEDRON, V65, P805
[5]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[6]   The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes [J].
Basavaiah, D ;
Sharada, DS ;
Kumaragurubaran, N ;
Reddy, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7135-7137
[7]   A novel and facile synthesis of functionalized [4.4.3] and [4.4.4] propellano-bislactones using acetates of the Baylis-Hillman adducts [J].
Basavaiah, D ;
Satyanarayana, T .
ORGANIC LETTERS, 2001, 3 (23) :3619-3622
[8]   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
[9]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[10]   PHOSPHINE MEDIATED SYNTHESIS OF 2-METHYLIDENE-3-AMINO ESTERS AND KETONES [J].
BERTENSHAW, S ;
KAHN, M .
TETRAHEDRON LETTERS, 1989, 30 (21) :2731-2732