Temporary in situ aluminum and zinc tethering in Diels-Alder reactions

被引:36
作者
Bertozzi, F
Olsson, R
Frejd, T
机构
[1] ACADIA Pharmaceut AS, Synthet Chem, DK-2600 Glostrup, Denmark
[2] Univ Lund, Dept Chem, S-22100 Lund, Sweden
关键词
D O I
10.1021/ol0057232
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Temporary tethering using aluminum or zinc in Diels-Alder reactions made possible the use of otherwise "noncompatible" combinations of dienes and dienophiles, resulting in the one-step formation of substituted cyclohexene 1,2-bis-methanols. Excellent regioselectivity and also significant stereoselectivity were obtained.
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页码:1283 / 1286
页数:4
相关论文
共 18 条
[1]   Alkenylboronate tethered intramolecular Diels-Alder reactions [J].
Batey, RA ;
Thadani, AN ;
Lough, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :450-451
[2]   SILICON-TETHERED REACTIONS [J].
BOLS, M ;
SKRYDSTRUP, T .
CHEMICAL REVIEWS, 1995, 95 (05) :1253-1277
[3]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL TRIENES - THE EFFECT ON STEREOSELECTIVITY OF ALLYLIC SUBSTITUTION [J].
CRAIG, D ;
READER, JC .
TETRAHEDRON LETTERS, 1992, 33 (28) :4073-4076
[4]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL TRIENES - DIENOPHILE-CONTROLLED CYCLOADDITIONS OF MATCHED AND UNMATCHED DIMETHYLATED SUBSTRATES [J].
CRAIG, D ;
READER, JC .
TETRAHEDRON LETTERS, 1992, 33 (41) :6165-6168
[5]  
Fensterbank L, 1997, SYNTHESIS-STUTTGART, P813
[6]   Disposable tethers in synthetic organic chemistry [J].
Gauthier, DR ;
Zandi, KS ;
Shea, KJ .
TETRAHEDRON, 1998, 54 (11) :2289-2338
[7]  
HASLINGER E, 1989, LIEBIGS ANN CHEM, P121
[8]  
Maruoka K, 1999, CHEM-EUR J, V5, P829, DOI 10.1002/(SICI)1521-3765(19990301)5:3<829::AID-CHEM829>3.3.CO
[9]  
2-S
[10]  
NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1171