Effective asymmetric epoxidation of Styrenes by chiral dioxirane

被引：47

作者：

Goeddel, D ^{[1
]}

Shu, LH ^{[1
]}

Yuan, Y ^{[1
]}

Wong, A ^{[1
]}

Wang, B ^{[1
]}

Shi, Y ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 04期

关键词：

D O I：

10.1021/jo0520285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High enantio selectivity (80-92% enantiomeric excess (ee)) has been obtained for the epoxidation of various styrenes using an easily prepared ketone (4) catalyst.

引用

页码：1715 / 1717

页数：3

共 50 条

[1] Catalytic asymmetric synthesis of epoxides mediated by chiral iminium salts [J].

Aggarwal, VK ;

Wang, MF .

CHEMICAL COMMUNICATIONS, 1996, (02) :191-192

[2] Absolute configuration of α-methylstyrene oxide:: The correct absolute configuration/optical rotation correlation [J].

Archelas, A ;

Furstoss, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6112-6114

[3] Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone [J].

Armstrong, A ;

Hayter, BR .

CHEMICAL COMMUNICATIONS, 1998, (05) :621-622

[4] Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxides [J].

Berkessel, A ;

Frauenkron, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16) :2265-2266

[5] Oxygen atom transfer from a chiral oxaziridinium salt.: Asymmetric epoxidation of unfunctionalized olefins. [J].

Bohé, L ;

Lusinchi, M ;

Lusinchi, X .

TETRAHEDRON, 1999, 55 (01) :141-154

[6] A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes [J].

Chan, WK ;

Yu, WY ;

Che, CM ;

Wong, MK .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6576-6582

[7] THREITOL-STRAPPED MANGANESE PORPHYRINS AS ENANTIOSELECTIVE EPOXIDATION CATALYSTS OF UNFUNCTIONALIZED OLEFINS [J].

COLLMAN, JP ;

LEE, VJ ;

KELLENYUEN, CJ ;

ZHANG, XM ;

IBERS, JA ;

BRAUMAN, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) :692-703

[8] 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

[9] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[10] CHEMISTRY OF OXAZIRIDINES .4. ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED ALKENES USING CHIRAL 2-SULFONYLOXAZIRIDINES - EVIDENCE FOR A PLANAR TRANSITION-STATE GEOMETRY [J].

DAVIS, FA ;

HARAKAL, ME ;

AWAD, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (10) :3123-3126

← 1 2 3 4 5 →