New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis

被引:78
作者
El-Qisairi, AK [1 ]
Qaseer, HA [1 ]
Katsigras, G [1 ]
Lorenzi, P [1 ]
Trivedi, U [1 ]
Tracz, S [1 ]
Hartman, A [1 ]
Miller, JA [1 ]
Henry, PM [1 ]
机构
[1] Loyola Univ, Dept Chem, Chicago, IL 60626 USA
关键词
D O I
10.1021/ol0273093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The oxidation of olefins by chiral monometallic and bimetallic Pd(II)-Cu(II) catalysts in bromide-containing aqueous-THF reaction mixtures produced chiral 1,2-dibromides. With alpha-olefins, the ee's were about 95% while most of the internal alkenes gave somewhat lower enantioselectivities (similar to80%).
引用
收藏
页码:439 / 441
页数:3
相关论文
共 11 条
[1]  
BRUNNER O, 1954, MONATSH CHEM, V85, P915
[2]   Oxidation of olefins by palladium(II) Part 17. An asymmetric chlorohydrin synthesis catalyzed by a bimetallic palladium(II) complex [J].
El-Qisairi, A ;
Henry, PM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (01) :50-60
[3]   A new palladium(II)-catalyzed asymmetric chlorohydrin synthesis [J].
El-Qisairi, A ;
Hamed, O ;
Henry, PM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2790-2791
[4]  
ELQISIARI AK, 2000, J ORGANOMET CHEM, V656, P167
[5]   SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .22. NEW APPROACH TO STRYCHNOS ALKALOIDS - STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].
FEVIG, JM ;
MARQUIS, RW ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5085-5086
[6]   BICYCLOANNULATION OF ALPHA-BROMO ALPHA,BETA-UNSATURATED ESTERS - SYNTHESIS OF THE TRICYCLO[4.4.0.0(1,5)]DECANE FRAMEWORK AND ITS CONGENERS [J].
HAGIWARA, H ;
ABE, F ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2651-2655
[7]   Oxidation of olefins by palladium(II). 16. A new palladium(II)-catalyzed asymmetric chlorohydrin synthesis [J].
Hamed, O ;
Henry, PM .
ORGANOMETALLICS, 1998, 17 (23) :5184-5189
[8]  
HENRY PM, 1980, PALLADIUM CATALYZED, P73
[9]   THE COMPOUNDS RELATED TO 3-(1-IMIDAZOLYL)-2-ALKEN-1-ONES - PREPARATION AND REACTIONS [J].
KASHIMA, C ;
TAJIMA, T ;
OMOTE, Y .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (01) :171-175
[10]   A new route to functionalised π-allyltricarbonyliron lactam complexes from aziridines and their use in stereoselective synthesis and oxidative conversion to β-lactams [J].
Ley, SV ;
Middleton, B .
CHEMICAL COMMUNICATIONS, 1998, (18) :1995-1996