Copper-catalyzed olefin epoxidation by dioxygen or amine N-oxide

被引：18

作者：

Rousselet, G ^{[1
]}

Chassagnard, C ^{[1
]}

Capdevielle, P ^{[1
]}

Maumy, M ^{[1
]}

机构：

[1] CNRS,ESPCI,RECH ORGAN LAB,F-75231 PARIS 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 47期

关键词：

D O I：

10.1016/0040-4039(96)01976-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The O-2/(CuOAc)-O-I system oxidizes initially tetrahydropyridines 1a, b into the corresponding epoxides 2a, b. Epoxide 2b is also formed by reaction of tetrahydropyridine N-oxide db with Cu-II(OAc)(2), providing evidence for active copper-oxygen species as common intermediates in these epoxidizing systems. Subsequent Cu-II - promoted regioselective opening of epoxides 2a,b is studied. Copyright (C) 1996 Elsevier Science Ltd

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页码：8497 / 8500

页数：4

相关论文

共 19 条

[1] CONFORMATIONAL-ANALYSIS OF INTRAMOLECULAR HYDROGEN-BONDED AMINO-ALCOHOLS - DETERMINATION OF NH-N-ELECTRON PAIR EQUILIBRIUM AND ASSIGNMENT OF CONFORMATIONAL FREE-ENERGIES FOR INTERACTIONS IN DECAHYDROQUINOLINE AND PIPERIDINE COMPOUNDS IN A DILUTE NONPOLAR MEDIUM [J].

AARON, HS ;

FERGUSON, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) :7013-7017

[2] MECHANISM OF THE COPPER MEDIATED OXIDATION OF PRIMARY ALIPHATIC-AMINES BY THE CU0/02 ACETIC-ACID SYSTEM IN ACETONITRILE [J].

CAPDEVIELLE, P ;

LAVIGNE, A ;

MAUMY, M .

TETRAHEDRON, 1990, 46 (08) :2835-2844

[3]

CAROLING G, 1988, INDIAN J CHEM A, V27, P873

[4]

CHRISTL M, 1971, J AM CHEM SOC, V93, P3463, DOI 10.1021/ja00743a028

[5] NICKEL(II) AND COPPER(II) COMPLEXES WITH AMIDRAZONE-BASED LIGANDS - STRUCTURE AND CATALYTIC ACTIVITY [J].

GERBELEU, NV ;

PALANCIUC, SS ;

SIMONOV, YA ;

DVORKIN, AA ;

BOUROSH, PN ;

REETZ, MT ;

ARION, VB ;

TOLLNER, K .

POLYHEDRON, 1995, 14 (04) :521-527

[6]

GOTTLIEB HE, 1979, J CHEM RES M, P4055

[7] SYNTHESIS AND CHEMISTRY OF 5,6-DIHYDROPYRIDINIUM SALT ADDUCTS - SYNTHONS FOR GENERAL ELECTROPHILIC AND NUCLEOPHILIC-SUBSTITUTION OF THE PIPERIDINE RING-SYSTEM [J].

GRIERSON, DS ;

HARRIS, M ;

HUSSON, HP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :1064-1082

[8] ALKALOID FORMATION THROUGH N-OXIDE INTERMEDIATES - REGIOSELECTIVE SYNTHESIS OF (+/-)-CORYTUBERINE BY REDOX REACTION [J].

KAMETANI, T ;

IHARA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02) :629-632

[9] CONFORMATIONAL STUDY OF 1,2,2,6,6-PENTAMETHYL-4-PHENYL-4-PIPERIDINOL [J].

LYLE, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (10) :1280-1281

[10] AEROBIC OXIDATIONS OF ALKANES AND ALKENES IN THE PRESENCE OF ALDEHYDES CATALYZED BY COPPER-SALTS [J].

MURAHASHI, SI ;

ODA, Y ;

NAOTA, T ;

KOMIYA, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :139-140