Establishing cleavage conditions for an anthracene chiral auxiliary using a photochemical retro Diels-Alder reaction

被引:26
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
基金
英国工程与自然科学研究理事会;
关键词
Diels-Alder; retro Diels-Alder; diastereoselective cycloaddition;
D O I
10.1016/S0040-4039(02)02255-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photochemical Diels-Alder additions of chiral 9-anthranyl ethanol derivatives have been conducted giving rise to addition adducts in reasonable yield and excellent diastereoselectivity. Thermal and photochemical retro Diels-Alder additions have also been achieved providing a facile cleavage method for use of this compound Lis a new chiral auxiliary. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9097 / 9100
页数:4
相关论文
共 7 条
[1]   Mechanistic investigations in diastereoselective Diels-Alder additions of chiral 9-anthrylethanol derivatives [J].
Atherton, JCC ;
Jones, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (19) :2166-2173
[2]   Diastereomeric control of photoinduced Diels-Alder reactions of 1-anthracen-9-yl-ethanol by hydrogen-bonding effects [J].
Atherton, JCC ;
Jones, S .
TETRAHEDRON LETTERS, 2001, 42 (46) :8239-8241
[3]   Photodimerization of anthracenes in fluid solution: structural aspects [J].
Bouas-Laurent, H ;
Castellan, A ;
Desvergne, JP ;
Lapouyade, R .
CHEMICAL SOCIETY REVIEWS, 2000, 29 (01) :43-55
[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]  
KAUPP G, 1977, LIEBIGS ANN CHEM, P254
[6]  
LASNE MC, 1985, SYNTHESIS-STUTTGART, P121
[7]   Stereoselective Diels-Alder reactions of chiral anthracenes [J].
Sanyal, A ;
Snyder, JK .
ORGANIC LETTERS, 2000, 2 (16) :2527-2530