AN INTRAMOLECULAR DIELS-ALDER REACTION OF VINYLSILANES

被引:57
作者
SIEBURTH, SM
FENSTERBANK, L
机构
[1] Department of Chemistry, State University of New York, New York 11794-3400, Stony Brook
关键词
D O I
10.1021/jo00046a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dialkylvinylsilyl ethers of dienols undergo a smooth intramolecular Diels-Alder reaction to Yield a versatile bicyclic product with an endo-exo selectivity influenced by the substituents on silicon.
引用
收藏
页码:5279 / 5281
页数:3
相关论文
共 48 条
[1]   1,3-ASYMMETRIC VERSUS 1,2-ASYMMETRIC INDUCTION IN THE REDUCTION OF BETA-HYDROXY KETONES BY INTRAMOLECULAR HYDROSILYLATION [J].
ANWAR, S ;
BRADLEY, G ;
DAVIS, AP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1383-1389
[2]   SILAHETEROCYCLES .3. SYNTHESIS AND REACTIVITY OF DI-TERT-BUTYLNEOPENTYLSILAETHENE, BU-TERT-2 SI=CHCH2BU-TERT [J].
AUNER, N .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1988, 558 (03) :87-106
[3]   STERIC EFFECTS - A STUDY OF A RATIONALLY DESIGNED SYSTEM [J].
BOTT, G ;
FIELD, LD ;
STERNHELL, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) :5618-5626
[4]   DIENOPHILIC PROPERTIES OF PHENYL VINYL SULFONE AND TRANS-1-(PHENYLSULFONYL)-2-(TRIMETHYLSILYL)ETHYLENE - THEIR UTILIZATION AS SYNTHONS FOR ETHYLENE, 1-ALKENES, ACETYLENE, AND MONOSUBSTITUTED ALKYNES IN THE CONSTRUCTION OF FUNCTIONALIZED 6-MEMBERED RINGS VIA [4 + 2] PI-CYCLOADDITION METHODOLOGY [J].
CARR, RVC ;
WILLIAMS, RV ;
PAQUETTE, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4976-4986
[5]  
Carruthers W., 1990, CYCLOADDITION REACTI
[6]  
COLVIN EW, 1987, CHEM METAL CARBON BO, V4, P539
[7]   A NOVEL STRATEGY FOR REGIOCONTROL AND STEREOCONTROL IN [4+2] CYCLOADDITIONS - INTRAMOLECULAR DIELS-ALDER REACTION OF A SILYL ACETAL TRIENE [J].
CRAIG, D ;
READER, JC .
TETRAHEDRON LETTERS, 1990, 31 (45) :6585-6588
[9]  
CUNICO RF, 1971, ORGANOMET CHEM SYNTH, V1, P253
[10]   HETERODIENE SYNTHESES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
DESIMONI, G ;
TACCONI, G .
CHEMICAL REVIEWS, 1975, 75 (06) :651-692