Diastereomeric control of photoinduced Diels-Alder reactions of 1-anthracen-9-yl-ethanol by hydrogen-bonding effects

被引：34

作者：

Atherton, JCC ^{[1
]}

Jones, S ^{[1
]}

机构：

[1] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 46期

关键词：

anthracene; auxiliary; diastereocontrol; Diels-Alder; hydrogen bonding; photochemistry;

D O I：

10.1016/S0040-4039(01)01742-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoinduced Diels-Alder reactions of 1-anthracen-9-yl-ethanol with maleic anhydride proceed with high diastereoselection but with complete reversal of the sense of selectivity compared to analogous O compound, Hydrogen-bonding effects have been established as the predominant factors in determining this selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8239 / 8241

页数：3

共 7 条

[1] Regioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with 2,4-hexadien-1-ol [J].

Araya-Maturana, R ;

Cassels, BK ;

Delgado-Castro, T ;

Valderrama, JA ;

Weiss-López, BE .

TETRAHEDRON, 1999, 55 (03) :637-648

[2] Modelling of solvent effects on the Diels-Alder reaction [J].

Cativiela, C ;

Garcia, JI ;

Mayoral, JA ;

Salvatella, L .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (03) :209-&

[3] STEREOSELECTIVE CONTROL IN 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO SUBSTITUTED STYRENES [J].

CHIACCHIO, U ;

CASUSCELLI, F ;

CORSARO, A ;

RESCIFINA, A ;

ROMEO, G ;

UCCELLA, N .

TETRAHEDRON, 1994, 50 (22) :6671-6680

[4] Highly diastereoselective photochemical Diels-Alder reactions: towards the development of a photoactivated chiral auxiliary [J].

Jones, S ;

Atherton, JCC .

TETRAHEDRON-ASYMMETRY, 2001, 12 (08) :1117-1119

[5]

PIMENTEL GC, 1960, HYDROGEN BOND, P255

[6] Stereoselective Diels-Alder reactions of chiral anthracenes [J].

Sanyal, A ;

Snyder, JK .

ORGANIC LETTERS, 2000, 2 (16) :2527-2530

[7] ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL DIENES - CONTROL OF FACIAL SELECTIVITY THROUGH HYDROGEN-BONDING [J].

TRIPATHY, R ;

CARROLL, PJ ;

THORNTON, ER .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6743-6744

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