Eco-friendly heterogeneous solid acids as novel and recyclable catalysts in ionic medium for tetrahydropyranols

被引:72
作者
Yadav, JS [1 ]
Reddy, BVS [1 ]
Reddy, MS [1 ]
Niranjan, N [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
solid acids; homoallyl alcohols; tetrahydropyranols;
D O I
10.1016/j.molcata.2003.08.024
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A variety of aldehydes and homoallylic alcohols undergo smoothly Prins-cyclization on the surface of solid acids such as H-ZSM-5 zeolite or Amberlyst-15(R) ion-exchange resin in 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid to afford the corresponding tetrahydropyranols in high yields with cis-diastereoselectivity. The recovered ionic liquid containing solid acid was recycled in subsequent runs without loss of activity. (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码:99 / 103
页数:5
相关论文
共 19 条
[1]  
ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661
[2]   LEWIS ACID MEDIATED CONDENSATION OF ALKENOLS AND ALDEHYDES - A SELECTIVE SYNTHESIS OF TETRAHYDROPYRANS AND OXEPANES [J].
COPPI, L ;
RICCI, A ;
TADDEI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :911-913
[3]   Direct formation of tetrahydropyranols via catalysis in ionic liquid [J].
Keh, CCK ;
Namboodiri, VV ;
Varma, RS ;
Li, CJ .
TETRAHEDRON LETTERS, 2002, 43 (28) :4993-4996
[4]  
Nicolaou K.C., 1996, Classics in Total Synthesis
[5]   SYNTHESIS OF 4-HETERO-SUBSTITUTED PYRANOSIDES VIA DIOXENIUM CATION-OLEFIN CYCLIZATION [J].
PERRON, F ;
ALBIZATI, KF .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4128-4130
[6]   Organic transformations using zeolites and zeotype materials [J].
Sen, SE ;
Smith, SM ;
Sullivan, KA .
TETRAHEDRON, 1999, 55 (44) :12657-12698
[7]   Catalytic reactions in ionic liquids [J].
Sheldon, R .
CHEMICAL COMMUNICATIONS, 2001, (23) :2399-2407
[8]  
Wasserscheid P, 2000, ANGEW CHEM INT EDIT, V39, P3772, DOI 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO
[9]  
2-5
[10]   LEWIS ACID PROMOTED CONDENSATION OF ALLYLALKOXYSILANES WITH CARBONYL-COMPOUNDS - SYNTHESIS OF TETRAHYDROPYRANS [J].
WEI, ZY ;
WANG, D ;
LI, JS ;
CHAN, TH .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5768-5774