Efficient Propargylation of Aldehydes and Ketones Catalyzed by Titanocene(III)

被引:53
作者
Justicia, Jose [1 ]
Sancho-Sanz, Iris [1 ]
Alvarez-Manzaneda, Enrique [1 ]
Enrique Oltra, J. [1 ]
Cuerva, Juan M. [1 ]
机构
[1] Univ Granada, Dept Organ Chem, Fac Sci, E-18071 Granada, Spain
关键词
homogeneous catalysis; propargylation; synthetic methods; titanium; EPOXYPOLYENE CYCLIZATION; STRAIGHTFORWARD SYNTHESIS; ORGANIC-SYNTHESIS; ALLENIC ALCOHOLS; TI-III; RADICALS; ADDITIONS; TERPENOIDS; REAGENTS; EPOXIDES;
D O I
10.1002/adsc.200900479
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We describe a novel method for the propargylation of a wide range of aldehydes and ketones catalyzed by titanocene(III) complexes under mild reaction conditions and compatible with many functional groups. Homopropargylic alcohols are obtained as the sole products even when ketones are used as starting materials, which is unusual in Barbier-type propargylations.
引用
收藏
页码:2295 / 2300
页数:6
相关论文
共 84 条
[1]  
ARCAYA HP, 2007, ORG LETT, V9, P3535
[2]   The first catalytic enantioselective Nozaki-Hiyama-Kishi reaction [J].
Bandini, M ;
Cozzi, PG ;
Umani-Ronchi, A .
POLYHEDRON, 2000, 19 (05) :537-539
[3]   Unified synthesis of eudesmanolides, combining biomimetic strategies with homogeneous catalysis and free-radical chemistry [J].
Barrero, AF ;
Rosales, A ;
Cuerva, JM ;
Oltra, JE .
ORGANIC LETTERS, 2003, 5 (11) :1935-1938
[4]   PREPARATION OF POLYFUNCTIONAL ALLENIC ALCOHOLS BY THE REGIOSELECTIVE ADDITION OF FUNCTIONALIZED PROPARGYLIC CHROMIUM(III) ORGANOMETALLICS TO CARBONYL-COMPOUNDS [J].
BELYK, K ;
ROZEMA, MJ ;
KNOCHEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4070-4074
[5]  
Blomberg C., 1993, The Barbier reaction and related one-step processes
[6]  
Campana A. G., 2008, ANGEW CHEM, V120, P7625
[7]   Divergent titanium-mediated allylations with modulation by nickel or palladium [J].
Campana, Araceli G. ;
Bazdi, Btissam ;
Fuentes, Noelia ;
Robles, Rafael ;
Cuerva, Juan M. ;
Oltra, J. Enrique ;
Porcel, Susana ;
Echavarren, Antonio M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7515-7519
[8]   ADDITIONS OF CHIRAL ALLYLTITANOCENES TO ALDEHYDES - DIASTEREOSELECTIVE SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH A RECYCLABLE CHIRAL TRANSITION-METAL REAGENT [J].
COLLINS, S ;
KUNTZ, BA ;
HONG, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4154-4158
[9]   Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond [J].
Cozzi, PG ;
Hilgraf, R ;
Zimmermann, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4095-4105
[10]  
Cuerva J. M., 2006, ANGEW CHEM, V118, P5648, DOI DOI 10.1002/ANGE.200600831