Asymmetric allylic oxidation of cycloalkenes using a tridentate tris(oxazoline) ligand as a chiral auxiliary

被引:84
作者
Kohmura, Y [1 ]
Katsuki, T [1 ]
机构
[1] Kyushu Univ 33, Grad Sch Sci, Dept Mol Chem, Higashi Ku, Fukuoka 8128581, Japan
关键词
tris(oxazoline) ligand; asymmetric allylic oxidation;
D O I
10.1016/S0040-4039(00)00522-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tridentate tris(oxazoline) ligand (4b) was found to be an efficient chiral auxiliary for copper-mediated asymmetric allylic oxidation (Kharash-Sosnovsky reaction) of cycloalkenes. Regardless of the ring size of the substrate, the reaction examined showed good enantioselectivity higher than 81% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3941 / 3945
页数:5
相关论文
共 23 条
[1]   THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE [J].
ANDRUS, MB ;
ARGADE, AB ;
CHEN, X ;
PAMMENT, MG .
TETRAHEDRON LETTERS, 1995, 36 (17) :2945-2948
[2]   Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants [J].
Andrus, MB ;
Chen, X .
TETRAHEDRON, 1997, 53 (48) :16229-16240
[3]   Asymmetric transformation of meso-epoxides by chiral lithium amides [J].
Asami, M .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1996, 54 (03) :188-199
[4]   Catalytic enantioselective allylic oxidation of olefins with copper complexes of chiral nonracemic bis(oxazolinyl)pyridine type ligands [J].
DattaGupta, A ;
Singh, VK .
TETRAHEDRON LETTERS, 1996, 37 (15) :2633-2636
[5]   A CONVENIENT METHOD FOR PREPARATION OF SOME OPTICALLY ACTIVE ALLYLIC ALCOHOLS [J].
DENNEY, DB ;
NAPIER, R ;
CAMMARAT.A .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) :3151-&
[6]   ENANTIOSELECTIVE ALLYLIC OXIDATION CATALYZED BY CHIRAL BISOXAZOLINE-COPPER COMPLEXES [J].
GOKHALE, AS ;
MINIDIS, ABE ;
PFALTZ, A .
TETRAHEDRON LETTERS, 1995, 36 (11) :1831-1834
[7]  
KATSUKI T, 1999, ASYMMETRIC C H OXIDA, V2, P791
[8]  
KAWASAKI K, 1995, SYNLETT, P1245
[9]   Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst [J].
Kawasaki, K ;
Katsuki, T .
TETRAHEDRON, 1997, 53 (18) :6337-6350
[10]   THE REACTIONS OF TERT-BUTYL PERBENZOATE AND OLEFINS - A STEREOSPECIFIC REACTION [J].
KHARASCH, MS ;
SOSNOVSKY, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (03) :756-756