Effects of Methyl Substituents on the Activity and Enantioselectivity of Homobenzotetramisole-Based Catalysts in the Kinetic Resolution of Alcohols

被引：64

作者：

Zhang, Yuhua ^{[1
]}

Birman, Vladimir B. ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 14-15期

关键词：

acylation; catalyst design; kinetic resolution; organocatalysis; MANNICH REACTION; ORGANIC-SYNTHESIS; ACYLATION; BENZOTETRAMISOLE; DERIVATIVES; ALDEHYDES; IMINES; ESTERS;

D O I：

10.1002/adsc.200900383

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Substitution of the tetrahydropyrimidine ring in the enantioselective acyl transfer catalyst homobenzotetramisole (HBTM) 6 with methyl groups exerts a dramatic influence on its performance in the kinetic resolution of secondary alcohols. The syn-3-methyl analogue of HBTM (9a) has proved to be superior to the parent compound in terms of catalytic activity, enantioselectivity, and synthetic accessibility.

引用

收藏

页码：2525 / 2529

页数：5

相关论文

共 30 条

[11] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :542-547

[12] The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes [J].

Hayashi, Y ;

Tsuboi, W ;

Ashimine, I ;

Urushima, T ;

Shoji, M ;

Sakai, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3677-3680

[13]

Hayashi Y., 2003, ANGEW CHEM, V115, P3805

[14]

Kagan H. B., 1998, TOPICS STEREOCHEMIST, V18, P249

[15] Enantioselective acylation of secondary alcohols catalyzed by chiral N-heterocyclic carbenes [J].

Kano, T ;

Sasaki, K ;

Maruoka, K .

ORGANIC LETTERS, 2005, 7 (07) :1347-1349

[16] Kinetic resolution of racemic alcohols catalyzed by minimal artificial acylases derived from L-histidine [J].

Kosugi, Yuji ;

Akakura, Matsujiro ;

Ishihara, Kazuaki .

TETRAHEDRON, 2007, 63 (27) :6191-6203

[17] In search of peptide-based catalysts for asymmetric organic synthesis [J].

Miller, SJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :601-610

[18] Concise synthesis of spirocyclic, bridged γ-butyrolactones via stereospecific, dyotropic Rearrangements of β-lactones involving 1,2-acyl and δ-lactone migrations [J].

Purohit, Vikrarn C. ;

Matla, Andrea S. ;

Romo, Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) :10478-+

[19] Kinetic Resolution of Racemic Carboxylic Acids Using Achiral Alcohols by the Promotion of Benzoic Anhydrides and Tetramisole Derivatives: Production of Chiral Nonsteroidal Anti-Inflammatory Drugs and Their Esters [J].

Shiina, Isamu ;

Nakata, Kenya ;

Onda, Yu-suke .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (35) :5887-5890

[20] Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline [J].

Terakado, D ;

Koutaka, H ;

Oriyama, T .

TETRAHEDRON-ASYMMETRY, 2005, 16 (06) :1157-1165