A study of epoxyolefin cyclizations catalyzed by bismuth trifluoromethanesulfonate and other metal triflates

被引：30

作者：

Lacey, JR ^{[1
]}

Anzalone, PW ^{[1
]}

Duncan, CM ^{[1
]}

Hackert, MJ ^{[1
]}

Mohan, RS ^{[1
]}

机构：

[1] Illinois Wesleyan Univ, Dept Chem, Lab Environm Friendly Organ Synth, Bloomington, IL 61701 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 49期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/j.tetlet.2005.10.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8507 / 8511

页数：5

共 57 条

[1] PHOTOCHEMICAL-REACTIONS .117. PHOTOCHEMISTRY OF 5,6-EPOXYDIENES AND OF CONJUGATED 5,6-EPOXYTRIENES [J].

ALDER, AP ;

WOLF, HR ;

JEGER, O .

HELVETICA CHIMICA ACTA, 1981, 64 (01) :198-214

[2] Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate [J].

Anderson, ED ;

Ernat, JJ ;

Nguyen, MP ;

Palma, AC ;

Mohan, RS .

TETRAHEDRON LETTERS, 2005, 46 (45) :7747-7750

[3]

[Anonymous], CHEM ARSENIC ANTIMON

[4] Bismuth(III) tris(trifluoromethanesulfonate) [J].

Antoniotti, S .

SYNLETT, 2003, (10) :1566-1567

[5] Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate [J].

Anzalone, PW ;

Baru, AR ;

Danielson, EM ;

Hayes, PD ;

Nguyen, MP ;

Panico, AF ;

Smith, RC ;

Mohan, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2091-2096

[6] SYNTHESIS OF (+/-)-KARAHANA ETHER AND A (+/-)-LABDADIENOIC ACID BY THE ELECTROPHILIC CYCLIZATION OF EPOXY ALLYLSILANES [J].

ARMSTRONG, RJ ;

WEILER, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (03) :584-596

[7] Bismuth compounds in organic synthesis. Deprotection of ketoximes using bismuth bromide-bismuth triflate [J].

Arnold, JN ;

Hayes, PD ;

Kohaus, RL ;

Mohan, RS .

TETRAHEDRON LETTERS, 2003, 44 (51) :9173-9175

[8] A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate [J].

Bhatia, KA ;

Eash, KJ ;

Leonard, NM ;

Oswald, MC ;

Mohan, RS .

TETRAHEDRON LETTERS, 2001, 42 (46) :8129-8132

[9] LEWIS ACID-INDUCED CYCLIZATION OF VINYL ETHER EPOXIDES - NEW STEREOSPECIFIC ROUTE TO CARBOCYCLIC KETONES AND KETOLACTONES [J].

BOECKMAN, RK ;

BRUZA, KJ ;

HEINRICH, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) :7101-7103

[10]

Brezinski B., 1991, J CHEM SOC P2, V2, P857

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