The double annulation of tethered diacids and alkynones: History and scope

被引:27
作者
Grossman, RB [1 ]
机构
[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
关键词
bicyclic compounds; Michael additions; annulations; aminations; acylations;
D O I
10.1055/s-2001-9690
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The double Michael reaction of a tethered carbon diacid (a 1,n-dinucleophile) with an alkynone (a 1,1-dielectrophile) provides highly substituted and functionalized monocyclic double Michael adducts in what is formally an [n+1] annulation. The pendant functionality in the double Michael adduct can be used to effect a second annulation. A history and overview of the "double annulation" route to bicyclic compounds is presented. The scope and selectivity of the route is also discussed.
引用
收藏
页码:13 / 21
页数:9
相关论文
共 35 条
[1]   CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .8. SYNTHESIS OF HYDROXYDIHYDROFURAN ACETAL FRAGMENTS FOR BIOLOGICAL EVALUATION AND AZADIRACHTIN TOTAL SYNTHESIS STUDIES [J].
ANDERSON, JC ;
LEY, SV ;
SANTAFIANOS, D ;
SHEPPARD, RN .
TETRAHEDRON, 1991, 47 (33) :6813-6850
[2]  
[Anonymous], 1987, MECH THEORY ORGANIC
[3]   CYCLIC DIENES .8. 1,2-DIMETHYLENECYCLOPENTANE [J].
BAILEY, WJ ;
SORENSON, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (21) :5421-5423
[4]  
BARON H, 1904, J CHEM SOC, P1736
[5]  
BEST SR, 1909, J CHEM SOC, P685
[6]  
BHARDWAJ CL, 1977, TETRAHEDRON, V33, P3279
[7]   RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].
BOWDEN, K ;
HEILBRON, IM ;
JONES, ERH ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45
[8]  
BRITTENKELLY M, 1980, SYNTHESIS-STUTTGART, P27
[9]  
CARPENTER HCH, 1899, J CHEM SOC, V75, P921
[10]  
Cope A. C., 1941, J AM CHEM SOC, V63, P733, DOI DOI 10.1021/JA01848A025