Zn(salen)-catalyzed asymmetric alkynylation of ketones

被引:55
作者
Saito, B [1 ]
Katsuki, T [1 ]
机构
[1] Kyushu Univ, Fac Sci, Grad Sch, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan
关键词
Zn(salen) complex; asymmetric catalysis; asymmetric alkynylation; ketone; tertiary propargylic alcohol;
D O I
10.1055/s-2004-829057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An in situ generated Zn complex of salen ligand 4 was found to serve as an efficient catalyst for asymmetric addition reaction of an alkynylzinc reagent to various ketones. For example, addition of phenylacetylene to 3,3-dimethyl-2-butanone using the Zn complex as catalyst showed enantioselectivity as high as 91 % ee.
引用
收藏
页码:1557 / 1560
页数:4
相关论文
共 35 条
[1]  
[Anonymous], J AM CHEM SOC
[2]   The diversity observed in manganese(III) complexes of tetradentate Schiff base ligands: An assessment of structural trends [J].
Bermejo, MR ;
Fondo, M ;
GarciaDeibe, A ;
Rey, M ;
Sanmartin, J ;
Sousa, A ;
Watkinson, M ;
McAuliffe, CA ;
Pritchard, RG .
POLYHEDRON, 1996, 15 (23) :4185-4194
[3]   Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3611-3612
[4]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[5]   Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes [J].
Cozzi, PG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2895-2898
[6]   Enantioselective addition of Et(2)Zn to aldehydes promoted by a chiral Schiff base metal complex [J].
Cozzi, PG ;
Papa, A ;
UmaniRonchi, A .
TETRAHEDRON LETTERS, 1996, 37 (26) :4613-4616
[7]   Development of bifunctional salen catalysts:: Rapid, chemoselective alkylations of α-ketoesters [J].
DiMauro, EF ;
Kozlowski, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12668-12669
[8]   Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes [J].
DiMauro, EF ;
Kozlowski, MC .
ORGANIC LETTERS, 2001, 3 (19) :3053-3056
[9]   Catalytic asymmetric addition of ZnPh2 to ketones:: Enantioselective formation of quaternary stereocenters [J].
Dosa, PI ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :445-446
[10]   Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1806-1807