A Mesoporous-Silica-Immobilized Oxovanadium Cocatalyst for the Lipase-Catalyzed Dynamic Kinetic Resolution of Racemic Alcohols

被引：100

作者：

Egi, Masahiro ^{[1
]}

Sugiyama, Koji ^{[1
]}

Saneto, Moriaki ^{[1
]}

Hanada, Ryosuke ^{[1
]}

Kato, Katsuya ^{[2
]}

Akai, Shuji ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

[2] Natl Inst Adv Ind Sci & Technol, Moriyama Ku, Nagoya, Aichi 4638560, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 13期

关键词：

alcohols; dynamic kinetic resolution; lipases; mesoporous silica; vanadium; HYDROGEN-TRANSFER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; SECONDARY ALCOHOLS; TRANSITION-METAL; RACEMIZATION; AMINES; ENZYME; ROUTE; ACIDS; IMPERANENE;

D O I：

10.1002/anie.201208988

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

V for resolution: A new oxovanadium catalyst (V-MPS; see scheme) immobilized in the pores of mesoporous silica has been developed. The combined use of V-MPS and lipases achieved the dynamic kinetic resolution of a wide range of racemic alcohols (1 or 2) to produce optically active esters 3 in high chemical and optical yields. The paired catalysts retained high catalytic activity when reused up to six times. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3654 / 3658

页数：5

共 51 条

[1] Racemization catalysts for the dynamic kinetic resolution of alcohols and amines [J].

Ahn, Yangsoo ;

Ko, Soo-Byung ;

Kim, Mahn-Joo ;

Park, Jaiwook .

COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :647-658

[2] A dynamic kinetic esolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3] [J].

Akai, S ;

Tanimoto, K ;

Kanao, Y ;

Egi, M ;

Yanamoto, T ;

Kita, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2592-2595

[3]

Akai S., 2006, ANGEW CHEM, V118, P2654

[4] One-Pot Synthesis of Optically Active Allyl Esters via Lipase-Vanadium Combo Catalysis [J].

Akai, Shuji ;

Hanada, Ryosuke ;

Fujiwara, Noboru ;

Kita, Yasuyuki ;

Egi, Masahiro .

ORGANIC LETTERS, 2010, 12 (21) :4900-4903

[5] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[6]

[Anonymous], 2010, ANGEW CHEM

[7] Transition metal hydrides as active intermediates in hydrogen transfer reactions [J].

Bäckvall, JE .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 652 (1-2) :105-111

[8] Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis [J].

Baer, Katrin ;

Krausser, Marina ;

Burda, Edyta ;

Hummel, Werner ;

Berkessel, Albrecht ;

Groeger, Harald .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9355-9358

[9] Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer-Schuster and Rupe rearrangements to redox isomerizations [J].

Cadierno, Victorio ;

Crochet, Pascale ;

Garcia-Garrido, Sergio E. ;

Gimeno, Jose .

DALTON TRANSACTIONS, 2010, 39 (17) :4015-4031

[10] Enantioselective synthesis of imperanene via enzymatic asymmetrization of an intermediary 1,3-diol [J].

Carr, JA ;

Bisht, KS .

ORGANIC LETTERS, 2004, 6 (19) :3297-3300

← 1 2 3 4 5 6 →