Stereoselective Diels-Alder reaction of electrogenerated quinones on a PTFE-fiber coated electrode in lithium perchlorate nitromethane

被引：24

作者：

Chiba, K ^{[1
]}

Jinno, M ^{[1
]}

Kuramoto, R ^{[1
]}

Tada, M ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Bioorgan Chem Lab, Fuchu, Tokyo 1838509, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(98)01090-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reaction of dienes and in situ generated quinones was accelerated on a PTFE-fit,er in an electrolytic lithium perchlorate / nitromethane system. In the presence of PTFE-fiber on a glassy carbon electrode, unstable quinones were efficiently generated by electrooxidation and trapped by dienes maintained on the poly-fluorinated fiber to give the desired cycloadducts stereoselectively in excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5527 / 5530

页数：4

共 7 条

[1] Synthesis of euglobal-G3 and -G4
Chiba, K
Arakawa, T
Tada, M
[J]. CHEMICAL COMMUNICATIONS, 1996, (15) : 1763 - 1764
[2] INTERMOLECULAR CYCLOADDITION REACTION OF UNACTIVATED ALKENES AND O-QUINONE METHIDES GENERATED BY ELECTROCHEMICAL OXIDATION - A PROPOSED BIOMIMETIC APPROACH TO THE EUGLOBAL SKELETONS
CHIBA, K
SONOYAMA, J
TADA, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) : 1381 - 1382
[3] Electrochemical synthesis of chroman and euglobal skeletons via cycloaddition reaction of o-quinone methides and alkenes
Chiba, K
Sonoyama, J
Tada, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12): : 1435 - 1443
[4] DIELS-ALDER REACTION OF QUINONES GENERATED IN-SITU BY ELECTROCHEMICAL OXIDATION IN LITHIUM PERCHLORATE-NITROMETHANE
CHIBA, K
TADA, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (21) : 2485 - 2486
[5] THE LITHIUM PERCHLORATE-DIETHYL ETHER RATE ACCELERATION OF THE DIELS-ALDER REACTION - LEWIS ACID CATALYSIS BY LITHIUM ION
FORMAN, MA
DAILEY, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) : 2761 - 2762
[6] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED
GRIECO, PA
NUNES, JJ
GAUL, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4595 - 4596
[7] AZA DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTION - CYCLOCONDENSATION OF DIENES WITH SIMPLE IMINIUM SALTS GENERATED UNDER MANNICH CONDITIONS
LARSEN, SD
GRIECO, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) : 1768 - 1769

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