Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones

被引:156
作者
Huang, Y [1 ]
Rawal, VH [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
D O I
10.1021/ja0267627
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the first examples of hydrogen-bond-promoted acceleration of hetero-Diels-Alder reactions and the use of such catalysis for the hetero-Diels-Alder reactions of simple, unactivated ketones. Several spiro-fused dihydropyans were synthesized in good yields using this procedure. This activation protocol represents an attractive and operationally simple alternative to conventional, Lewis acid catalysis. Copyright © 2002 American Chemical Society.
引用
收藏
页码:9662 / 9663
页数:2
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共 30 条
[1]  
Bednarski M.D., 1991, COMPREHENSIVE ORGANI, V2, P661, DOI DOI 10.1016/B978-0-08-052349-1.00044-5
[2]  
BOGER DL, 1987, HETERO DIELSALDER ME, V47
[3]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[4]   A CONVENIENT SYNTHESIS OF 3,4-BIS(TRIMETHYLSILYLMETHYL)-5,6-DIHYDRO-2H-PYRANS THROUGH A CATALYZED HETERO-DIELS-ALDER REACTION [J].
BROUARD, C ;
PORNET, J ;
MIGINIAC, L .
SYNTHETIC COMMUNICATIONS, 1994, 24 (21) :3047-3053
[5]   A novel synthesis of 1-isochromanols via hetero Diels-Alder reaction of carbonyl compounds with 1-trimethylsilyloxy-benzocyclobutene as a precursor of alpha-oxy-o-quinodimethane under mild condition [J].
Chino, K ;
Takata, T ;
Endo, T .
SYNTHETIC COMMUNICATIONS, 1996, 26 (11) :2145-2154
[6]   HIGH-PRESSURE APPROACH TO THE TOTAL SYNTHESIS OF (+/-)-AMBREINOLIDE AND (+/-)-8-EPIAMBREINOLIDE [J].
DANIEWSKI, WM ;
KUBAK, E ;
JURCZAK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :3963-3965
[7]  
DANISHEFSKY SJ, 1987, ANGEW CHEM INT EDIT, V15, P5
[8]  
Green R. D., 1974, HYDROGEN BONDING C H
[9]  
Grieco P. A., 1991, ALDRICHIM ACTA, V24, P59
[10]   REACTIONS OF KETENE ACETALS .15. REGIOSPECIFIC SYNTHESES OF ERYTHROLACCIN AND 7-HYDROXYERYTHROLACCIN [J].
GUAY, V ;
BRASSARD, P .
TETRAHEDRON, 1984, 40 (24) :5039-5045