Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution

被引:112
作者
Rho, Ho Sik [2 ,3 ]
Oh, Sang Ho [3 ]
Lee, Ji Woong [3 ]
Lee, Jin Yong [3 ]
Chin, Jik [1 ]
Song, Choong Eui [3 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 1A1, Canada
[2] AmorePacific Corp, R&D Ctr, Yongin 446729, South Korea
[3] Sungkyunkwan Univ, Dept Chem, Suwon 440746, Gyeonggi, South Korea
关键词
D O I
10.1039/b719811f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly enantioselective methanolysis of meso-cyclic anhydride was achieved with bifunctional organocatalyst containing a quinine-thiourea moiety; unusual concentration, temperature and solvent effects on the enantioselectivity can be explained in terms of a mechanism involving monomer-dimer equilibration of the catalyst.
引用
收藏
页码:1208 / 1210
页数:3
相关论文
共 24 条
[1]   CATALYTIC ASYMMETRIC-SYNTHESIS OF HIGHLY FUNCTIONALIZED COMPOUNDS WITH 6 CONTIGUOUS STEREOCENTERS [J].
AITKEN, RA ;
GOPAL, J ;
HIRST, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :632-634
[2]   Stereoselective anhydride openings [J].
Atodiresei, Luliana ;
Schiffers, Ingo ;
Bolm, Carsten .
CHEMICAL REVIEWS, 2007, 107 (12) :5683-5712
[3]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[4]   A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines [J].
Bode, Christiane M. ;
Ting, Amal ;
Schaus, Scott E. .
TETRAHEDRON, 2006, 62 (49) :11499-11505
[5]   Practical and highly enantioselective ring opening of cyclic meso-anhydrides mediated by cinchona alkaloids [J].
Bolm, C ;
Schiffers, I ;
Dinter, CL ;
Gerlach, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :6984-6991
[6]   An alkaloid-mediated desymmetrization of meso-anhydrides via a nucleophilic ring opening with benzyl alcohol and its application in the synthesis of highly enantiomerically enriched β-amino acids [J].
Bolm, C ;
Schiffers, I ;
Atodiresei, I ;
Hackenberger, CPR .
TETRAHEDRON-ASYMMETRY, 2003, 14 (22) :3455-3467
[7]  
Bolm C, 1999, SYNLETT, P195
[8]   ASYMMETRIC ALCOHOLYSIS OF MESO-ANHYDRIDES MEDIATED BY ALKALOIDS (Bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid, 3-endo-benzyloxycarbonyl, (2R,3S)-) [J].
Bolm, Carsten ;
Atodiresei, Iuliana ;
Schiffers, Ingo .
ORGANIC SYNTHESES, 2005, 82 :120-+
[9]   A highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids [J].
Chen, YG ;
Tian, SK ;
Deng, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9542-9543
[10]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175