Natural cyclic α,β-enone monoterpenoids in nucleophilic addition reactions

被引:4
作者
Ishmuratov, G. Yu.
Kharisov, R. Ya.
Latypova, E. R.
Talipov, R. F.
机构
[1] Russian Acad Sci, Inst Organ Chem, Ufa Sci Ctr, Ufa 450054, Russia
[2] Bashkir State Univ, Ufa 450074, Russia
关键词
organometallic reagents; natural cyclic alpha; beta-enone monoterpenoids; Michael reaction; 1,2-and 1,4-addition reactions;
D O I
10.1007/s10600-006-0161-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The literature on transformations of natural cyclic alpha,beta-enone monoterpenoids into compounds of more complicated structure via 1,2- and 1,4-addition reactions was reviewed. The data were systematized according to the effects of the conditions and nature of the starting substrates on the selectivity of the 1,2- and 1,4-addition reactions.
引用
收藏
页码:367 / 388
页数:22
相关论文
共 82 条
[1]  
ALAMI M, 1997, ORG SYNTH, V72, P135
[2]   SYNTHESIS OF ISOSHYOBUNONE [J].
ALEXANDRE, C ;
ROUESSAC, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (08) :275-276
[3]   ORGANOMETALLIC REACTION-MECHANISMS .14. ROLE OF TRANSITION-METAL CATALYSTS IN FORMATION OF AROMATIC PINACOLS AND HYDROLS DURING GRIGNARD-REAGENT ADDITION TO KETONES [J].
ASHBY, EC ;
BUHLER, JD ;
LOPP, IG ;
WIESEMANN, TL ;
BOWERS, JS ;
LAEMMLE, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6561-6570
[4]   Stereospecific intramolecular Michael addition to (-)-carvone based on temporary sulfur connection [J].
Bachi, MD ;
Bilokin, YV ;
Melman, A .
TETRAHEDRON LETTERS, 1998, 39 (19) :3035-3038
[5]   ORGANOALUMINUM COMPOUNDS .29. NICKEL-CATALYZED CONJUGATE ADDITION OF TRIMETHYLALUMINUM TO ALPHA,BETA-UNSATURATED KETONES [J].
BAGNELL, L ;
JEFFERY, EA ;
MEISTERS, A ;
MOLE, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (04) :801-815
[6]   DIENEDIOLATES FROM UNSATURATED CARBOXYLIC-ACIDS - MICHAEL ADDITION OF DILITHIUM BUTA-1,3-DIENE-1,1-DIOLATE (FROM CROTONIC ACID) TO UNSATURATED-KETONES [J].
BALLESTER, P ;
COSTA, A ;
RASO, AG ;
GOMEZSOLIVELLAS, A ;
MESTRES, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1711-1717
[7]  
BOYER BJ, 1981, J CHEM SOC CHEM COMM, P122
[8]  
BUSCHMANN H, 1988, SYNTHESIS-STUTTGART, P827
[9]   ORGANOMANGANESE (II) REAGENTS .16. COPPER-CATALYZED 1,4-ADDITION OF ORGANOMANGANESE CHLORIDES TO CONJUGATED ENONES [J].
CAHIEZ, G ;
ALAMI, M .
TETRAHEDRON LETTERS, 1989, 30 (27) :3541-3544
[10]  
CASEY CP, 1979, J AM CHEM SOC, V101, P4236, DOI 10.1021/ja00509a033