Catalytic asymmetric addition of dimethylzinc to α-ketoesters, using mandelamides as ligands

被引:52
作者
Blay, G [1 ]
Fernández, I [1 ]
Marco-Aleixandre, A [1 ]
Pedro, JR [1 ]
机构
[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain
关键词
D O I
10.1021/ol052997m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A strategy based on the control of the electron-donating capabilities of the coordinating groups of the ligand has been applied in the catalytic asymmetric addition of organometallic reagents to ketoesters. Mandelamides having deprotonated alcohol and carboxyamido groups catalyzed the addition of dimethylzinc to alpha-ketoesters with good yields and ee (up to 90%).
引用
收藏
页码:1287 / 1290
页数:4
相关论文
共 43 条
[11]   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
[12]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters [J].
Evans, DA ;
Burgey, CS ;
Kozlowski, MC ;
Tregay, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :686-699
[13]   Mechanism and scope of salen bifunctional catalysts in asymmetric aldehyde and α-ketoester alkylation [J].
Fennie, MW ;
DiMauro, EF ;
O'Brien, EM ;
Annamalai, V ;
Kozlowski, MC .
TETRAHEDRON, 2005, 61 (26) :6249-6265
[14]   2-piperidino-1,1,2-triphenylethanol:: A highly effective catalyst for the enantioselective arylation of aldehydes [J].
Fontes, M ;
Verdaguer, X ;
Solà, L ;
Pericàs, MA ;
Riera, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2532-2543
[15]   Multicenter strategy for the development of catalytic enantioselective nucleophilic alkylation of ketones:: Me2Zn addition to α-ketoesters [J].
Funabashi, K ;
Jachmann, M ;
Kanai, M ;
Shibasaki, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5489-5492
[16]   A practical catalytic asymmetric addition of alkyl groups to ketones [J].
García, C ;
LaRochelle, LK ;
Walsh, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :10970-10971
[17]   Enantioselective addition of dimethylzinc to aldehydes:: assessment of optimal N,N-substitution for 2-dialkylamino-1,1,2-triphenylethanol ligands [J].
García-Delgado, N ;
Fontes, M ;
Pericàs, MA ;
Riera, A ;
Verdaguer, X .
TETRAHEDRON-ASYMMETRY, 2004, 15 (13) :2085-2090
[18]   Asymmetric hetero Diels-Alder route to quaternary carbon centers: synthesis of (-)-malyngolide [J].
Ghosh, AK ;
Shirai, M .
TETRAHEDRON LETTERS, 2001, 42 (36) :6231-6233
[19]  
Haas K, 1998, ANGEW CHEM INT EDIT, V37, P1086, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1086::AID-ANIE1086>3.0.CO
[20]  
2-V