Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

被引：58

作者：

Kuroboshi, M ^{[1
]}

Yoshihisa, H ^{[1
]}

Cortona, MN ^{[1
]}

Kawakami, Y ^{[1
]}

Gao, Z ^{[1
]}

Tanaka, H ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 42期

关键词：

kinetic resolution; electrochemistry; oxidation; alcohols;

D O I：

10.1016/S0040-4039(00)01419-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electro-oxidative kinetic resolution of sec-alcohols mediated with a catalytic amount of an optically active N-oxyl was performed by use of a simple undivided cell under constant current conditions. The selectivity factor (S-value) increased remarkably when the reaction was performed at lower temperatures. The optically active N-oxyl was recovered and used repeatedly without any change in efficiency and selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8131 / 8135

页数：5

共 12 条

[1] Biocatalytic oxidative kinetic resolution of sec-alcohols:: stereocontrol through substrate-modification
Stampfer, W
Kosjek, B
Faber, K
Kroutil, W
TETRAHEDRON-ASYMMETRY, 2003, 14 (02) : 275 - 280
[2] Autoamplification-Enhanced Oxidative Kinetic Resolution of sec-Alcohols and Alkyl Mandelates, and its Kinetic Model
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[3] Enzymatic kinetic resolution of sec-alcohols using an ionic liquid anhydride as acylating agent
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TETRAHEDRON-ASYMMETRY, 2014, 25 (12) : 944 - 948
[4] Dynamic kinetic resolution of aromatic sec-alcohols by using a heterogeneous palladium racemization catalyst and lipase
Xu, Yuanfeng
Wang, Meng
Feng, Bo
Li, Ziyang
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Li, Hexing
Li, Hui
CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (04) : 5838 - 5842
[5] Kinetic resolution of sec-alcohols and axially chiral biaryls using novel fluxionally chiral DMAP catalysts
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[6] One-pot preparation of optically active sec-alcohols, epoxides, and sulfoxides by a combination of synthesis and enantiomeric resolution with optically active hosts in a water suspension medium
Miyamoto, H
Yasaka, S
Takaoka, R
Tanaka, K
Toda, F
ENANTIOMER, 2001, 6 (01): : 51 - 55
[7] Enantioselective electrocatalytic oxidation of racemic sec-alcohols using a chiral 1-azaspiro[5.5]undecane-N-oxyl radical
Kashiwagi, Y
Kurashima, F
Kikuchi, C
Anzai, J
Osa, T
Bobbitt, JM
TETRAHEDRON LETTERS, 1999, 40 (35) : 6469 - 6472
[8] Rapid, room-temperature acylative kinetic resolution of sec-alcohols using atropisomeric 4-aminopyridine/triphenylphosphine catalysis
Spivey, AC
Arseniyadis, S
Fekner, T
Maddaford, A
Leese, DP
TETRAHEDRON, 2006, 62 (2-3) : 295 - 301
[9] Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues
Dalaigh, CO
Hynes, SJ
Maher, DJ
Connon, SJ
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (06) : 981 - 984
[10] Kinetic Resolution of Racemic Secondary Alcohols Mediated by N-Methylimidazole in the Presence of Optically Active Acyl Chlorides
Leclercq, Loic
Suisse, Isabelle
Agbossou-Niedercorn, Francine
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (14) : 2696 - 2700

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