Biomimetic and organocatalytic approaches to oxidation catalysis

被引：22

作者：

Berkessel, A ^{[1
]}

机构：

[1] Univ Cologne, Dept Organ Chem, D-50939 Cologne, Germany

来源：

PURE AND APPLIED CHEMISTRY | 2005年 / 77卷 / 07期

关键词：

biomimetic oxidation catalysis; organocatalysis; amino acids; asymmetric epoxidation; cyclopropanation; C-C coupling; dynamic kinetic resolution; Ru-porphyrins; DIANANE; Nozaki-Hiyama-Kishi coupling;

D O I：

10.1351/pac200577071277

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The lecture summarized our recent work in the fields of (i) catalytic asymmetric epoxidation and cyclopropanation, (ii) C-C coupling reactions, and (iii) dynamic kinetic resolution (DKR). The first section describes the use of chiral Ru-porphyrins as catalysts for the asymmetric epoxidation and cyclopropanation of nonfunctionalized olefins, and of peptides and alkaloid-based phase-transfer catalysts for the asymmetric epoxidation of enones. The second section highlights the application of the DIANANE-salen ligands (DIANANE: endo,endo-2,5-diamino-norbornane) to the asymmetric Nozaki-Hiyama-Kishi coupling of aldehydes with allylic and vinylic electrophiles, and of N-tosyl proline amides for asymmetric aldol additions. In the final section, bifunctional urea-based organocatalysts for the DKR of azlactones to provide enantiomerically enriched amino acid esters are presented.

引用

页码：1277 / 1284

页数：8

共 32 条

[1] Catalytic asymmetric epoxidation of enones under phase-transfer catalyzed conditions [J].

Arai, S ;

Tsuge, H ;

Oku, M ;

Miura, M ;

Shioiri, T .

TETRAHEDRON, 2002, 58 (08) :1623-1630

[2]

Arai S, 1998, SYNLETT, P1201

[3] Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxides [J].

Berkessel, A ;

Frauenkron, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16) :2265-2266

[4] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].

Berkessel, A ;

Cleemann, F ;

Mukherjee, S ;

Müller, TN ;

Lex, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811

[5] Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones [J].

Berkessel, A ;

Mukherjee, S ;

Cleemann, F ;

Müller, TN ;

Lex, J .

CHEMICAL COMMUNICATIONS, 2005, (14) :1898-1900

[6] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions [J].

Berkessel, A ;

Koch, B ;

Lex, J .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1141-1146

[7] Enantioselective synthesis of DIANANE, a novel C2-symmetric chiral diamine for asymmetric catalysis [J].

Berkessel, A ;

Schröder, M ;

Sklorz, CA ;

Tabanella, S ;

Vogl, N ;

Lex, J ;

Neudörfl, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3050-3056

[8] A highly enantioselective catalyst for the asymmetric Nozaki-Hiyama-Kishi reaction of allylic and vinylic halides [J].

Berkessel, A ;

Menche, D ;

Sklorz, CA ;

Schröder, M ;

Paterson, I .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :1032-+

[9] Highly enantioselective enone epoxidation catalyzed by short solid phase-bound peptides: Dominant role of peptide helicity [J].

Berkessel, A ;

Gasch, N ;

Glaubitz, K ;

Koch, C .

ORGANIC LETTERS, 2001, 3 (24) :3839-3842

[10]

BERKESSEL A, UNPUB

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