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

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 20期

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

页码：3941 / 3945

页数：5

共 23 条

[1] THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE
ANDRUS, MB
ARGADE, AB
CHEN, X
PAMMENT, MG
[J]. TETRAHEDRON LETTERS, 1995, 36 (17) : 2945 - 2948
[2] Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants
Andrus, MB
Chen, X
[J]. TETRAHEDRON, 1997, 53 (48) : 16229 - 16240
[3] Asymmetric transformation of meso-epoxides by chiral lithium amides
Asami, M
[J]. 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
DattaGupta, A
Singh, VK
[J]. TETRAHEDRON LETTERS, 1996, 37 (15) : 2633 - 2636
[5] A CONVENIENT METHOD FOR PREPARATION OF SOME OPTICALLY ACTIVE ALLYLIC ALCOHOLS
DENNEY, DB
NAPIER, R
CAMMARAT.A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) : 3151 - &
[6] ENANTIOSELECTIVE ALLYLIC OXIDATION CATALYZED BY CHIRAL BISOXAZOLINE-COPPER COMPLEXES
GOKHALE, AS
MINIDIS, ABE
PFALTZ, A
[J]. 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
Kawasaki, K
Katsuki, T
[J]. TETRAHEDRON, 1997, 53 (18) : 6337 - 6350
[10] THE REACTIONS OF TERT-BUTYL PERBENZOATE AND OLEFINS - A STEREOSPECIFIC REACTION
KHARASCH, MS
SOSNOVSKY, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (03) : 756 - 756

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