Montmorillonite-mediated hetero-Diels-Alder reaction of alkenes and o-quinomethanes generated in situ by dehydration of o-hydroxybenzyl alcohols

被引：57

作者：

Chiba, K ^{[1
]}

Hirano, T ^{[1
]}

Kitano, Y ^{[1
]}

Tada, M ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Bioorgan Chem Lab, Tokyo 1838503, Japan

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 08期

关键词：

D O I：

10.1039/a900657e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intermolecular herero-Diels-Alder reaction of in situ-generated o-quinomethanes and unactivated alkenes has been accomplished through a wet montmorillonite catalyst in a LiClO4-MeNO2 solution to give good yields of varied chromane skeletons.

引用

页码：691 / 692

页数：2

共 19 条

[1] STERIC AND ELECTRONIC FACTORS WHICH EFFECT THERMAL CYCLIZATION OF META-SUBSTITUTED ARYL PROPARGYL ETHERS - SYNTHESIS OF 5-SUBSTITUTED AND 7-SUBSTITUTED 3-CHROMENES [J].

ANDERSON, WK ;

LAVOIE, EJ ;

WHITKOP, PG .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :881-884

[2] ORTHO QUINONE METHIDES .2. TRAPPING WITH PRODUCTION OF CHROMANS [J].

BOLON, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3666-&

[3] SIMPLE METHODS FOR OXIDATION OF ORTHO-ALLYLPHENOLS TO CHROM-3-ENES [J].

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (19) :836-837

[4] TOTAL SYNTHESIS OF CARPANONE [J].

CHAPMAN, OL ;

ENGEL, MR ;

SPRINGER, JP ;

CLARDY, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (24) :6696-&

[5]

CHIA K, 1998, TETRAHEDRON LETT, V39, P9035

[6] Synthesis of euglobal-G3 and -G4 [J].

Chiba, K ;

Arakawa, T ;

Tada, M .

CHEMICAL COMMUNICATIONS, 1996, (15) :1763-1764

[7] INTERMOLECULAR CYCLOADDITION REACTION OF UNACTIVATED ALKENES AND O-QUINONE METHIDES GENERATED BY ELECTROCHEMICAL OXIDATION - A PROPOSED BIOMIMETIC APPROACH TO THE EUGLOBAL SKELETONS [J].

CHIBA, K ;

SONOYAMA, J ;

TADA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1381-1382

[8] Electrochemical synthesis of chroman and euglobal skeletons via cycloaddition reaction of o-quinone methides and alkenes [J].

Chiba, K ;

Sonoyama, J ;

Tada, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12) :1435-1443

[9]

CHIBA K, 1998, J CHEM SOC P1, V17, P2939

[10]

CORNIA M, 1977, GAZZ CHIM ITAL, V107, P299

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