Asymmetric Epoxidation of Conjugated Olefins with Dioxygen

被引:50
作者
Koya, Shota [1 ,2 ]
Nishioka, Yota [1 ,2 ]
Mizoguchi, Hirotaka [1 ,2 ]
Uchida, Tatsuya [1 ,2 ]
Katsuki, Tsutomu [1 ,2 ]
机构
[1] Kyushu Univ, Grad Sch, Fac Sci, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan
[2] Kyushu Univ, Int Inst Carbon Neutral Energy Res WPI I2CNER, Higashi Ku, Fukuoka 8128581, Japan
关键词
aerobic oxidation; asymmetric catalysis; dioxygen; epoxidation; ruthenium; WATER-SOLUBLE METALLOPORPHYRINS; AEROBIC OXIDATION; KINETIC RESOLUTION; MOLECULAR-OXYGEN; COMPLEXES; PRECURSORS; IRON; DIHYDROXYLATION; AZIRIDINATION; TAUTOMERISM;
D O I
10.1002/anie.201201848
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A complex situation: Asymmetric epoxidation of conjugated olefins was achieved at room temperature using ruthenium complex 1 as the catalyst and air as the oxidant to give epoxides in up to 95 % ee (see scheme). When the product was acid sensitive, the reaction was carried out at 0 °C under oxygen. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8243 / 8246
页数:4
相关论文
共 39 条
[1]  
[Anonymous], ANGEW CHEM
[2]  
Anslyn E. V., 2006, MODERN PHYS ORGANIC
[3]   'Oxo-hydroxo tautomerism' as useful mechanistic tool in oxygenation reactions catalysed by water-soluble metalloporphyrins [J].
Bernadou, J ;
Meunier, B .
CHEMICAL COMMUNICATIONS, 1998, (20) :2167-2173
[4]   REDOX TAUTOMERISM IN HIGH-VALENT METAL-OXO-AQUO COMPLEXES - ORIGIN OF THE OXYGEN-ATOM IN EPOXIDATION REACTIONS CATALYZED BY WATER-SOLUBLE METALLOPORPHYRINS [J].
BERNADOU, J ;
FABIANO, AS ;
ROBERT, A ;
MEUNIER, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9375-9376
[5]   OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN [J].
BOLM, C ;
SCHLINGLOFF, G ;
WEICKHARDT, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18) :1848-1849
[6]  
Bolm C., 1994, ANGEW CHEM, V106, P1944
[7]   Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts:: Two faces of an FeIII-OOH coin [J].
Chen, K ;
Costas, M ;
Kim, JH ;
Tipton, AK ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :3026-3035
[8]   Dihydroxylation of olefins using air as the terminal oxidant [J].
Döbler, C ;
Mehltretter, GM ;
Sundermeier, U ;
Beller, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :70-76
[9]  
Döbler C, 1999, ANGEW CHEM INT EDIT, V38, P3026
[10]   Oxidation Catalysis of Nb(salan) Complexes: Asymmetric Epoxidation of Allylic Alcohols Using Aqueous Hydrogen Peroxide as an Oxidant [J].
Egami, Hiromichi ;
Oguma, Takuya ;
Katsuki, Tsutomu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) :5886-5895