Polymer-supported Lewis bases for the Baylis-Hillman reaction

被引:54
作者
Huang, JW [1 ]
Shi, M [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
acrylic esters; arenecarbaldehydes; Baylis-Hillman reaction; Lewis bases; methyl vinyl ketone (MVK); PEG(4600)-(PPh2)(2); polyDMAP; N-tosylimines (ArCH=NTs);
D O I
10.1002/adsc.200303072
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The use of polymer-supported Lewis bases such as PEG(4600)-(PPh2)(2) and poly(DMAP) in the Baylis-Hillman reactions of N-tosylimines (ArCH=NTs) 1 or the corresponding arenecarbaldehydes with alpha,beta-unsaturated ketones has been investigated. The corresponding Baylis-Hillman adducts are obtained in good yields. The polymer-supported Lewis bases can be easily recovered by filtration and the Lewis base PEG4600-(PPh2)(2) can be reproduced by reduction with LiAlH4 and CeCl3.
引用
收藏
页码:953 / 958
页数:6
相关论文
共 30 条
[1]   Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction.: Selective formation of α-methylene-β-amino acid derivatives [J].
Balan, D ;
Adolfsson, H .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2329-2334
[2]   Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].
Barrett, AGM ;
Cook, AS ;
Kamimura, A .
CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534
[3]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[4]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[5]  
Baylis A. B, 1972, German Patent, Patent No. 2155113
[6]   PHOSPHINE MEDIATED SYNTHESIS OF 2-METHYLIDENE-3-AMINO ESTERS AND KETONES [J].
BERTENSHAW, S ;
KAHN, M .
TETRAHEDRON LETTERS, 1989, 30 (21) :2731-2732
[7]  
BONORA GM, 1998, NUCLEOS NUCLEOT, V17, P1567
[8]  
Ciganek E., 1997, ORG REACTIONS, V51, P201
[9]  
GRAVERT DJ, 1997, CHEM REV, V97, P488
[10]  
Grether U, 2001, CHEM-EUR J, V7, P959, DOI 10.1002/1521-3765(20010302)7:5<959::AID-CHEM959>3.3.CO