A direct conversion of α,β-unsaturated ketones to vinylcyclopropanes:: new zirconium-mediated reaction

被引:18
作者
Bertus, P [1 ]
Gandon, V [1 ]
Szymoniak, J [1 ]
机构
[1] Univ Reims, F-51687 Reims 2, France
关键词
D O I
10.1039/a908897k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Various vinylcyclopropanes are synthesized from alpha,beta-unsaturated ketones via a zirconium-mediated [1,2]-addition-deoxygenative cyclopropanation sequence; the latter step surprisingly proceeds under specific protic conditions.
引用
收藏
页码:171 / 172
页数:2
相关论文
共 11 条
[1]   Titanium(IV) isopropoxide-catalysed reaction of alkylmagnesium halides with ethyl acetate in the presence of styrene. Non-hydride mechanism of ligand exchange in the titanacyclopropanes [J].
Epstein, OL ;
Savchenko, AI ;
Kulinkovich, OG .
TETRAHEDRON LETTERS, 1999, 40 (32) :5935-5938
[2]  
Höppe HA, 1998, ANGEW CHEM INT EDIT, V37, P1545, DOI 10.1002/(SICI)1521-3773(19980619)37:11<1545::AID-ANIE1545>3.0.CO
[3]  
2-3
[4]  
Hudlicky T., 1989, STUD NAT PROD CHEM B, V3, P3
[5]  
MURPHY PJ, 1995, COMPREHENSIVE ORGANI, V1, P801
[6]   PATTERNS OF STOICHIOMETRIC AND CATALYTIC REACTIONS OF ORGANOZIRCONIUM AND RELATED COMPLEXES OF SYNTHETIC INTEREST [J].
NEGISHI, E ;
TAKAHASHI, T .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (05) :124-130
[7]   Alkene and alkyne complexes of zirconocene. Their preparation, structure, and novel transformations [J].
Negishi, E ;
Takahashi, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (04) :755-769
[8]  
PAQUETTE LA, 1991, COMPREHENSIVE ORGANI, V5, P899
[9]   HIGHLY REGIOSELECTIVE REACTION OF ZIRCONOCENE-ALKENE COMPLEXES WITH ALDEHYDES OR KETONES [J].
SUZUKI, N ;
ROUSSET, CJ ;
AOYAGI, K ;
KOTORA, M ;
TAKAHASHI, T ;
HASEGAWA, M ;
NITTO, Y ;
SABURI, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 473 (1-2) :117-128
[10]   ZIRCONIUM MEDIATED REGIOSELECTIVE CARBON-CARBON BOND FORMATION REACTIONS [J].
TAKAHASHI, T ;
SUZUKI, N ;
HASEGAWA, M ;
NITTO, Y ;
AOYAGI, K ;
SABURI, M .
CHEMISTRY LETTERS, 1992, (02) :331-334