Reaction Rate Acceleration Enabled by Tethered Lewis Acid-Lewis Base Bifunctional Catalysis: A Catalytic, Enantioselective [2+2] Ketene Aldehyde Cycloaddition Reaction

被引：13
作者：
Chidara, Sridhar [1 ]
Lin, Yun-Ming [1 ]
机构：
[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA
来源：
SYNLETT | 2009年 / 10期
关键词：
Lewis acids; Lewis bases; bifunctional catalysts; rate acceleration; enantioselectivity; BETA-LACTONES; ASYMMETRIC-SYNTHESIS; DISUBSTITUTED KETENES; COMPLEXES; CHEMISTRY; ORGANOCATALYSIS; 2-OXETANONES; MECHANISM; SYSTEMS; LIGAND;
D O I：
10.1055/s-0029-1217332
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A tethered Lewis acid-Lewis base (LA*-LB*) bifunctional catalyst promotes the asymmetric [2+2] cycloaddition reaction between ketene and aldehydes rapidly. The LA*-LB* bifunctional catalyst, a quinine tethered Co(III)-salen complex (5 mol%) catalyzes the [2+2] cycloaddition reaction to produce the C4-substituted beta-lactones in uniformly >99% ee and high isolated yields (71-97%). The dramatic rate acceleration, the hallmark of cooperative intramolecular bifunctional catalysis, is achieved for the catalytic, enantioselective [2+2] cycloaddition reaction between aldehydes and unsubstituted ketene.
引用
收藏
页码：1675 / 1679
页数：5
相关论文
共 44 条
[1]   Formation of disubstituted β-lactones using bifunctional catalysis [J].
Calter, MA ;
Tretyak, OA ;
Flaschenriem, C .
ORGANIC LETTERS, 2005, 7 (09) :1809-1812
[2]  
Carreira E.M., 2006, ORG REACT, V67, P1, DOI DOI 10.1002/0471264180.OR067.01
[3]   CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].
CARREIRA, EM ;
SINGER, RA ;
LEE, WS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8837-8838
[4]   Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones [J].
Cortez, GS ;
Tennyson, RL ;
Romo, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7945-7946
[5]  
Denmark S.E., 2008, ANGEW CHEM, V120, P1584
[6]   Lewis base catalysis in organic synthesis [J].
Denmark, Scott E. ;
Beutner, Gregory L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638
[7]   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
[8]   C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes [J].
Evans, DA ;
Janey, JM .
ORGANIC LETTERS, 2001, 3 (13) :2125-2128
[9]   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
[10]   Chiral dirhodium(II) carboxamidate-catalyzed [2+2]-cycloaddition of TMS-ketene and ethyl glyoxylate [J].
Forslund, RE ;
Cain, J ;
Colyer, J ;
Doyle, MP .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :87-92
12345