Highly diastereoselective photochemical Diels-Alder reactions: towards the development of a photoactivated chiral auxiliary

被引：34

作者：

Jones, S ^{[1
]}

Atherton, JCC ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(01)00203-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Photochemical Diels-Alder additions uf maleic anhydride to a homochiral anthracene derivative occur with excellent diastereoselectivity (> 95:5) and faster than the corresponding thermal reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1117 / 1119

页数：3

共 10 条

[1] RETRODIENIC REACTIONS .17. A GENERAL-ROUTE TO ALLENES GEM-DIACTIVATED BY ELECTROATTRACTING GROUPS
HAKIKI, A
JABRY, Z
RIPOLL, JL
THUILLIER, A
[J]. TETRAHEDRON LETTERS, 1984, 25 (32) : 3461 - 3462
[2] HEMLCHEN G, 1987, TETRAHEDRON LETT, V28, P183
[3] Asymmetric reduction using N-methyl and N-benzyl oxazaborolidines based upon cis-1-amino-2-indanol:: a preliminary mechanistic study
Jones, S
Atherton, JCC
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (22) : 4543 - 4548
[4] KAUPP G, 1977, LIEBIGS ANN CHEM, P254
[5] EXTREMELY POWERFUL CHIRAL AUXILIARIES - ENANTIOMERIC [4+2] CYCLOADDUCTS OF 2-OXAZOLONE AND 9,10-DIMETHYLANTHRACENE
KIMURA, K
MURATA, K
OTSUKA, K
ISHIZUKA, T
HARATAKE, M
KUNIEDA, T
[J]. TETRAHEDRON LETTERS, 1992, 33 (31) : 4461 - 4464
[6] LASNE MC, 1985, SYNTHESIS-STUTTGART, P121
[7] MERRITT C, 1963, ORG SYNTH COLL 4, P8
[8] PROCTOR G, 1996, ASYMMETRIC SYNTHESIS
[9] Preparation of 1-(9-anthryl)-ethanol and 9-anthryloxirane via catalytic enantioselective reduction of prochiral 9-anthryl ketones
Reiners, I
Martens, J
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (01) : 27 - 28
[10] Stereoselective Diels-Alder reactions of chiral anthracenes
Sanyal, A
Snyder, JK
[J]. ORGANIC LETTERS, 2000, 2 (16) : 2527 - 2530

← 1 →