Oxidative kinetic resolution of racemic secondary alcohols catalyzed by resin supported sulfonato-Mn(salen) complex in water

被引：37

作者：

Kantam, M. Lakshmi ^{[1
]}

Ramani, T. ^{[1
]}

Chakrapani, L. ^{[1
]}

Choudary, B. M. ^{[1
]}

机构：

[1] Ogene Syst, Hyderabad 500037, Andhra Pradesh, India

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2007年 / 274卷 / 1-2期

关键词：

kinetic resolution; sulfonato-Mn(saten); complex; (R; R)-1; resin; PhI(OAc)(2); enantioselectivity (ee);

D O I：

10.1016/j.molcata.2007.04.020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The oxidative kinetic resolution of racemic secondary alcohols catalyzed by resin supported sulfonato-Mn(salen) complex (R,R)-1 with good to excellent ee's in water in the presence of diacetoxyiodobenzene (PhI(OAC)(2)) is described. The resin supported (R,R)-1 was recovered quantitatively by simple filtration and reused for three times with consistent activity. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：11 / 15

页数：5

共 46 条

[31] Catalytic asymmetric and chemoselective aerobic oxidation: kinetic resolution of sec-alcohols [J].

Masutani, K ;

Uchida, T ;

Irie, R ;

Katsuki, T .

TETRAHEDRON LETTERS, 2000, 41 (26) :5119-5123

[32] Kinetic resolution of alcohols catalyzed by tripeptides containing the N-alkylimidazole substructure [J].

Miller, SJ ;

Copeland, GT ;

Papaioannou, N ;

Horstmann, TE ;

Ruel, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1629-1630

[33] Dual role of (-)-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols [J].

Mueller, JA ;

Jensen, DR ;

Sigman, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8202-8203

[34] Extremely high enantioselective redox reaction of ketones and alcohols catalyzed by RuCl2(PPh3)(oxazolinylferrocenylphosphine) [J].

Nishibayashi, Y ;

Takei, I ;

Uemura, S ;

Hidai, M .

ORGANOMETALLICS, 1999, 18 (12) :2291-2293

[35] Nonenzymatic enantioselective acylation of racemic secondary alcohols catalyzed by a SnX(2)-chiral diamine complex [J].

Oriyama, T ;

Hori, Y ;

Imai, K ;

Sasaki, R .

TETRAHEDRON LETTERS, 1996, 37 (47) :8543-8546

[36] Dynamic kinetic resolution of secondary diols via coupled ruthenium and enzyme catalysis [J].

Persson, BA ;

Huerta, FF ;

Bäckvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5237-5240

[37] Ruthenium- and enzyme-catalyzed dynamic kinetic resolution of secondary alcohols [J].

Persson, BA ;

Larsson, ALE ;

Le Ray, M ;

Bäckvall, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (08) :1645-1650

[38] Polymer-supported (salen)Mn catalysts for asymmetric epoxidation: A comparison between soluble and insoluble matrices [J].

Reger, TS ;

Janda, KD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) :6929-6934

[39] Kinetic resolution of arylalkylcarbinols catalyzed by a planar-chiral derivative of DMAP: A new benchmark for nonenzymatic acylation [J].

Ruble, JC ;

Tweddell, J ;

Fu, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2794-2795

[40] Effective kinetic resolution of secondary alcohols with a planar-chiral analogue of 4-(dimethylamino)pyridine. Use of the Fe(C(5)Ph(5)) group in asymmetric catalysis [J].

Ruble, JC ;

Latham, HA ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1492-1493

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