Enantioselective oxidation of secondary alcohols catalyzed by soluble chiral polymeric [N′,N",bis(salicylidene)ethane-1,2-diaminato(2-)]manganese(III) ([MnIII(salen)] type complexes in a biphasic system

被引：23

作者：

Sun, Wei ^{[1
]}

Wu, Xiaomei ^{[1
]}

Xia, Chungu ^{[1
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

HELVETICA CHIMICA ACTA | 2007年 / 90卷 / 03期

关键词：

D O I：

10.1002/hlca.200790064

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The polymeric [N',N'-bis(salicylidene)ethane-1,2-diaminato(2-)]manganese(III) ([Mn-III(salen)]) type complexes 1 and 2 were successfully applied to the oxidative kinetic resolution of secondary alcohols. The reaction proceeded readily at room temperature with excellent enantioselectivities of up to 99.9% ee. A variety of substrates, including aromatic and aliphatic alcohols, could be tolerated. The polymeric catalysts could easily be recovered and recycled.

引用

页码：623 / 626

页数：4

共 27 条

[1] Palladium-catalyzed enantioselective oxidation of alcohols:: A dramatic rate acceleration by Cs2CO3/t-BuOH [J].

Bagdanoff, JT ;

Ferreira, EM ;

Stoltz, BM .

ORGANIC LETTERS, 2003, 5 (06) :835-837

[2] Soluble polymers as scaffolds for recoverable catalysts and reagents [J].

Dickerson, TJ ;

Reed, NN ;

Janda, KD .

CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343

[3] Recoverable catalysts for asymmetric organic synthesis [J].

Fan, QH ;

Li, YM ;

Chan, ASC .

CHEMICAL REVIEWS, 2002, 102 (10) :3385-3465

[4] The palladiuim-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen [J].

Ferreira, EM ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7725-7726

[5] Highly enantioselective benzylic hydroxylation with concave type of (salen)manganese(III) complex [J].

Hamada, T ;

Irie, R ;

Mihara, J ;

Hamachi, K ;

Katsuki, T .

TETRAHEDRON, 1998, 54 (34) :10017-10028

[6] Kinetic resolution of racemic secondary alcohols by Ru-II-catalyzed hydrogen transfer [J].

Hashiguchi, S ;

Fujii, A ;

Haack, KJ ;

Matsumura, K ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) :288-290

[7] Palladium-catalyzed enantioselective oxidations of alcohols using molecular oxygen [J].

Jensen, DR ;

Pugsley, JS ;

Sigman, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7475-7476

[8]

Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4

[9] Preparation of polymer-supported ligands and metal complexes for use in catalysis [J].

Leadbeater, NE ;

Marco, M .

CHEMICAL REVIEWS, 2002, 102 (10) :3217-3273

[10] Kinetic resolution of racemic secondary alcohols catalyzed by chiral diaminodiphosphine-Ir(I) complexes [J].

Li, Yan-Yun ;

Zhang, Xue-Qin ;

Dong, Zhen-Rong ;

Shen, Wei-Yi ;

Chen, Gui ;

Gao, Jing-Xing .

ORGANIC LETTERS, 2006, 8 (24) :5565-5567

← 1 2 3 →