Asymmetric Epoxidation of Olefins with Hydrogen Peroxide by an in Situ-Formed Manganese Complex

被引：33

作者：

Dai, Wen ^{[1
,2
,3
]}

Shang, Sensen ^{[1
,2
,3
]}

Chen, Bo ^{[1
,2
,3
]}

Li, Guosong ^{[1
,2
,3
]}

Wang, Lianyue ^{[1
,2
]}

Ren, Lanhui ^{[1
,2
,3
]}

Gao, Shuang ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 14期

关键词：

ELECTRON-DEFICIENT OLEFINS; NONHEME IRON CATALYSTS; ENANTIOSELECTIVE EPOXIDATION; SYSTEM HYDROGEN; TERMINAL OLEFINS; (L=1,4,7-TRIMETHYL-1,4,7-TRIAZACYCLONONANE)-OXALIC ACID; STEREOSELECTIVE EPOXIDATION; OXIDATION CATALYSIS; PORPHYRIN CATALYST; CARBOXYLIC ACID;

D O I：

10.1021/jo501178k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric epoxidation of a variety of cis, trans, terminal, and trisubstituted olefins in excellent yields (up to 94%) and enantioselectivities (>99% cc) by an in situ-formed manganese complex using H2O2 has been developed. A relationship between the hydrophobicity of the catalyst imposed by ligand and the catalytic activity has been observed. The influence of the amount and identity of the acid additive was examined, and improved enantioselectivities were achieved through the use of a catalytic amount of a carboxylic acid additive.

引用

页码：6688 / 6694

页数：7

共 47 条

[1] Electronically tuned chiral ruthenium porphyrins: Extremely stable and selective catalysts for asymmetric epoxidation and cyclopropanation [J].

Berkessel, A ;

Kaiser, P ;

Lex, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (19) :4746-4756

[2] Titanium Salalen Catalysts Based on cis-1,2-Diaminocyclohexane: Enantioselective Epoxidation of Terminal Non-Conjugated Olefins with H2O2 [J].

Berkessel, Albrecht ;

Guenther, Thomas ;

Wang, Qifang ;

Neudoerfl, Joerg-M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) :8467-8471

[3] PRACTICAL CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF PROPRANOLOL [J].

BEVINAKATTI, HS ;

BANERJI, AA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5372-5375

[4]

Bolm C, 1997, SYNLETT, P687

[5] A novel enantiopure proline-derived triazacyclononane:: synthesis, structure and application of its manganese complex [J].

Bolm, C ;

Meyer, N ;

Raabe, G ;

Weyhermüller, T ;

Bothe, E .

CHEMICAL COMMUNICATIONS, 2000, (24) :2435-2436

[6] MECHANISTIC STUDIES OF OLEFIN EPOXIDATION BY A MANGANESE PORPHYRIN AND HYPOCHLORITE - AN ALTERNATIVE EXPLANATION OF SATURATION KINETICS [J].

COLLMAN, JP ;

BRAUMAN, JI ;

HAMPTON, PD ;

TANAKA, H ;

BOHLE, DS ;

HEMBRE, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :7980-7984

[7] An efficient catalyst for asymmetric epoxidation of terminal olefins [J].

Collman, JP ;

Wang, Z ;

Straumanis, A ;

Quelquejeu, M ;

Rose, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :460-461

[8] Highly Stereoselective Epoxidation with H2O2 Catalyzed by Electron-Rich Aminopyridine Manganese Catalysts [J].

Cusso, Olaf ;

Garcia-Bosch, Isaac ;

Font, David ;

Ribes, Xavi ;

Lloret-Fillol, Julio ;

Costas, Miquel .

ORGANIC LETTERS, 2013, 15 (24) :6158-6161

[9] Asymmetric Epoxidation with H2O2 by Manipulating the Electronic Properties of Non-heme Iron Catalysts [J].

Cusso, Olaf ;

Garcia-Bosch, Isaac ;

Ribas, Xavi ;

Lloret-Fillol, Julio ;

Costas, Miquel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) :14871-14878

[10] Asymmetric Oxidation Catalysis by a Porphyrin-Inspired Manganese Complex: Highly Enantioselective Sulfoxidation with a Wide Substrate Scope [J].

Dai, Wen ;

Li, Jun ;

Chen, Bo ;

Li, Guosong ;

Lv, Ying ;

Wang, Lianyue ;

Gao, Shuang .

ORGANIC LETTERS, 2013, 15 (22) :5658-5661

← 1 2 3 4 5 →