Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether

被引：34

作者：

Akagawa, Kengo ^{[1
]}

Akabane, Hajime ^{[1
]}

Sakamoto, Seiji ^{[1
]}

Kudo, Kazuaki ^{[1
]}

机构：

[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 04期

关键词：

ENANTIOSELECTIVE TRANSFER HYDROGENATION; ORGANOCATALYTIC TRANSFER HYDROGENATION; ALPHA-IMINO ESTERS; ALDOL-REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL ADDITION; RECYCLABLE ORGANOCATALYST; REDUCTIVE AMINATION; ORGANIC-SYNTHESIS; PHOSPHORIC-ACID;

D O I：

10.1016/j.tetasy.2009.02.036

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A resin-supported N-terminal prolyl peptide having a beta-turn motif and a polyleucine tether has been developed for the organocatalytic asymmetric transfer hydrogenation under aqueous conditions. Polyleucine accelerated the reaction in a highly enantioselective manner by providing a hydrophobic microenvironment around the prolyl residue. The investigation of catalyst structures indicates that the L-form of polyleucine is essential for both reaction efficiency and enantioselectivity. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：461 / 466

页数：6

共 76 条

[61] Organocatalytic enantioselective reduction of Pyridines
Rueping, Magnus
Antonchick, Andrey P.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) : 4562 - 4565
[62] Remarkably low catalyst loading in Bronsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones
Rueping, Magnus
Antonchick, Andrey P.
Theissmann, Thomas
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) : 6751 - 6755
[63] A highly enantioselective bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids
Rueping, Magnus
Antonchick, Andrey R.
Theissmann, Thomas
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) : 3683 - 3686
[64] Dipeptide-catalyzed direct asymmetric aldol reaction
Shi, LX
Sun, Q
Ge, ZM
Zhu, YQ
Cheng, TM
Li, RT
[J]. SYNLETT, 2004, (12) : 2215 - 2217
[65] Enantioselective organocatalytic reductive amination
Storer, RI
Carrera, DE
Ni, Y
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 84 - 86
[66] Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: Unprecedented regiocontrol in aqueous media
Tang, Z
Yang, ZH
Cun, LF
Gong, LZ
Mi, AQ
Jiang, YZ
[J]. ORGANIC LETTERS, 2004, 6 (13) : 2285 - 2287
[67] Asymmetric catalysis by chiral hydrogen-bond donors
Taylor, MS
Jacobsen, EN
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) : 1520 - 1543
[68] (S)-Histidine-based dipeptides as organic catalysts for direct asymmetric aldol reactions
Tsogoeva, SB
Wei, SW
[J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (11) : 1947 - 1951
[69] Organocatalytic transfer hydrogenation of cyclic enones
Tuttle, Jamison B.
Ouellet, Stephane G.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12662 - 12663
[70] The peptide-catalyzed stereospecific synthesis of tetroses: A possible model for prebiotic molecular evolution
Weber, Arthur L.
Pizzarello, Sandra
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (34) : 12713 - 12717

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