Methyltrioxorhenium-Catalyzed Epoxidation of Homoallylic Alcohols with Hydrogen Peroxide

被引:11
作者
Yamazaki, Shigekazu [1 ]
机构
[1] Toyama Ind Technol Ctr, Takaoka, Toyama 9330981, Japan
关键词
CONTAINING DINUCLEAR PEROXOTUNGSTATE; MAIN-GROUP ELEMENTS; ASYMMETRIC EPOXIDATION; ALLYLIC ALCOHOLS; STEREOSELECTIVE EPOXIDATION; ASSISTED EPOXIDATION; ALKYLRHENIUM OXIDES; TRANSITION-METALS; BUFFERED MEDIA; MULTIPLE BONDS;
D O I
10.1021/jo301825j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homoallylic alcohols were efficiently converted to the corresponding 3,4-epoxy alcohols in excellent yields by methyltrioxorhenium (MTO)-catalyzed epoxidation with aqueous hydrogen peroxide as the terminal oxidant and 3-methylpyrazole (10 mol %) as an additive. The epoxidations of homoallylic alcohols proceeded under organic solvent-free conditions faster than those in dichloromethane.
引用
收藏
页码:9884 / 9888
页数:5
相关论文
共 48 条
[31]   Catalytic enantioselective epoxidation of homoallylic alcohols by chiral zirconium complexes [J].
Okachi, T ;
Murai, N ;
Onaka, M .
ORGANIC LETTERS, 2003, 5 (01) :85-87
[32]   EPOXIDATIONS WITH 30-PERCENT HYDROGEN-PEROXIDE CATALYZED BY TUNGSTIC ACID IN BUFFERED MEDIA [J].
PRAT, D ;
LETT, R .
TETRAHEDRON LETTERS, 1986, 27 (06) :707-710
[33]   STEREOSELECTIVE EPOXIDATION OF ALLYLIC AND HOMOALLYLIC ALCOHOLS WITH 30-PERCENT HYDROGEN-PEROXIDE CATALYZED BY TUNGSTIC ACID IN BUFFERED MEDIA [J].
PRAT, D ;
DELPECH, B ;
LETT, R .
TETRAHEDRON LETTERS, 1986, 27 (06) :711-714
[34]   Stereoselective VO(acac)2 catalyzed epoxidation of acyclic homoallylic diols. Complementary preparation of C2-syn-3,4-epoxy alcohols [J].
Rodriguez-Berrios, Raul R. ;
Torres, Gerardo ;
Prieto, Jose A. .
TETRAHEDRON, 2011, 67 (05) :830-836
[35]   ASYMMETRIC EPOXIDATION OF HOMOALLYLIC ALCOHOLS - SYNTHESIS OF (-)-GAMMA-AMINO-BETA(R)-HYDROXYBUTYRIC ACID (GABOB) [J].
ROSSITER, BE ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3707-3711
[36]   An Efficient and Selective Epoxidation of Olefins with Novel Methyltrioxorhenium/(Fluorous Ponytailed) 2,2′-Bipyridine Catalysts [J].
Saladino, Raffaele ;
Ginnasi, Maria Cristina ;
Collalto, Daniela ;
Bernini, Roberta ;
Crestini, Claudia .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) :1284-1290
[37]   Iron-Catalyzed Epoxidation of Aromatic Olefins and 1,3-Dienes [J].
Schroeder, Kristin ;
Enthaler, Stephan ;
Join, Benoit ;
Junge, Kathrin ;
Beller, Matthias .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1771-1778
[38]   HIGH STEREOSELECTIVITIES AND REGIOSELECTIVITIES IN TRANSITION-METAL CATALYZED EPOXIDATIONS OF OLEFINIC ALCOHOLS BY TERT-BUTYL HYDROPEROXIDE [J].
SHARPLES.KB ;
MICHAELS.RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) :6136-6137
[39]   Regioselective oxidative cyclization of hydroxyalkenes to tetrahydrofurans catalyzed by methyltrioxorhenium [J].
Tan, HS ;
Espenson, JH .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 152 (1-2) :83-89
[40]  
Tetzlaff HR, 1999, INORG CHEM, V38, P881