Intramolecular additions of alcohols and carboxylic acids to inert olefins catalyzed by silver(I) triflate

被引:159
作者
Yang, CG [1 ]
Reich, NW [1 ]
Shi, ZJ [1 ]
He, C [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
D O I
10.1021/ol051065f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular additions of hydroxyl or carboxyl groups to inert olefins catalyzed by simple silver(l) triflate are described. Good to excellent yields can be obtained for a range of substrates under relatively mild conditions. This reaction represents one of the simplest methods to construct cyclic ethers or lactones.
引用
收藏
页码:4553 / 4556
页数:4
相关论文
共 38 条
[1]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[2]   OLEFIN AND ACETYLENE COMPLEXES OF TRANSITION METALS [J].
BENNETT, MA .
CHEMICAL REVIEWS, 1962, 62 (06) :611-+
[3]  
BEVERWIJK CD, 1970, ORGANOMET CHEM REV A, V5, P215
[4]   New catalysts and conditions for a C-H insertion reaction identified by high throughput catalyst screening [J].
Burgess, K ;
Lim, HJ ;
Porte, AM ;
Sulikowski, GA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :220-222
[5]   Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes [J].
Cirakovic, J ;
Driver, TG ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9370-9371
[6]   Catalytic formation of C-O bonds by alkene activation:: Lewis acid-cycloisomerisation of olefinic alcohols [J].
Coulombel, L ;
Favier, I ;
Duñach, E .
CHEMICAL COMMUNICATIONS, 2005, (17) :2286-2288
[7]   Efficient aziridination of olefins catalyzed by a unique disilver(I) compound [J].
Cui, Y ;
He, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16202-16203
[8]   Chiral catalyst controlled diastereoselection and regioselection in intramolecular carbon-hydrogen insertion reactions of diazoacetates [J].
Doyle, MP ;
Kalinin, AV ;
Ene, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8837-8846
[9]   Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].
Ferraris, D ;
Young, B ;
Dudding, T ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549
[10]  
FISD HBT, 2004, ORGANOMETALLICS, V23, P1200