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

[31] EPOXY-SILANES IN ORGANIC-SYNTHESIS [J].

PROCTER, G ;

RUSSELL, AT ;

MURPHY, PJ ;

TAN, TS ;

MATHER, AN .

TETRAHEDRON, 1988, 44 (13) :3953-3973

[32] COPPER(I) CATALYSIS OF OLEFIN PHOTOREACTIONS .9. PHOTOBICYCLIZATION OF ALPHA-ALKENYLALLYL, BETA-ALKENYLALLYL, AND GAMMA-ALKENYLALLYL ALCOHOLS [J].

SALOMON, RG ;

COUGHLIN, DJ ;

GHOSH, S ;

ZAGORSKI, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) :998-1007

[33] TERPENE TERMINAL EPOXIDES . SKELETAL REARRANGEMENT ACCOMPANYING BICYCLIZATION OF SQUALENE 2,3-OXIDE [J].

SHARPLES.KB ;

VAN TAMELEN, EE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (07) :1848-+

[34] D,L-MALABARICANEDIOL - FIRST CYCLIC NATURAL PRODUCT DERIVED FROM SQUALENE IN A NONENZYMIC PROCESS [J].

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (23) :6999-+

[35] Facile and efficient method for the Prins reactions of styrenes and homoallyl alcohols to 1,3-dioxanes and 4-tetrahydropyranols using bismuth(III) triflate [J].

Sreedhar, B ;

Swapna, V ;

Sridhar, C ;

Saileela, D ;

Sunitha, A .

SYNTHETIC COMMUNICATIONS, 2005, 35 (09) :1177-1182

[36] Bismuth triflate and microencapsulated bismuth triflate: Efficient catalysts for methoxymethylation of alcohols and carboxylic acids [J].

Sreedhar, B ;

Swapna, V ;

Sridhar, C .

CATALYSIS COMMUNICATIONS, 2005, 6 (04) :293-296

[37] FURANS IN SYNTHESIS .3. FURANS AS TERMINATORS IN CATIONIC CYCLIZATION [J].

TANIS, SP ;

HERRINTON, PM .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4572-4580

[38] FURANS IN SYNTHESIS .8. FORMAL TOTAL SYNTHESES OF (+/-)-APHIDICOLIN AND (+)-APHIDICOLIN [J].

TANIS, SP ;

CHUANG, YH ;

HEAD, DB .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4929-4938

[39] CYCLIZATIONS WHEREIN AN EPOXIDE ACTS AS THE SOURCE OF INITIATION AND TERMINATION STEPS - EVIDENCE FOR AN EARLY TRANSITION-STATE IN BIOMIMETIC EPOXIDE CYCLIZATIONS [J].

TAYLOR, SK ;

MAY, SA ;

HOPKINS, JA .

TETRAHEDRON LETTERS, 1993, 34 (08) :1283-1286

[40] FRIEDEL-CRAFTS CYCLIALKYLATIONS OF SOME EPOXIDES .2. STEREOSPECIFICITY, SUBSTITUENT, PRODUCT, AND KINETIC-STUDIES [J].

TAYLOR, SK ;

DAVISSON, ME ;

HISSOM, BR ;

BROWN, SL ;

PRISTACH, HA ;

SCHRAMM, SB ;

HARVEY, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :425-429

← 1 2 3 4 5 6 →