Preparation and catalytic enantioselective reactions of C3-symmetric tris(oxazoline)s derived from Kemp's triacid

被引：18

作者：

Chuang, TH

Fang, JM ^{[1
]}

Bolm, C

机构：

[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan

[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

SYNTHETIC COMMUNICATIONS | 2000年 / 30卷 / 09期

关键词：

D O I：

10.1080/00397910008087200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kemp's triacid was elaborated to optically pure tris(beta-hydroxylamide)s and tris(oxazoline)s. The resulting C-3-symmetric compounds were used in diethylzinc additions to benzaldehyde and allylic oxidations of cyclopentene, based on Kharash reaction conditions, to give the corresponding products in good chemical yields and moderate enantioselectivities.

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页码：1627 / 1641

页数：15

相关论文

共 95 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] Efficient synthesis of 1,1′-binaphthyl and 2,2′-bi-o-tolyl-2,2′-bis(oxazoline)s and preliminary use for the catalytic asymmetric allylic oxidation of cyclohexene [J].

Andrus, MB ;

Asgari, D ;

Sclafani, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9365-9368

[3] MOLECULAR RECOGNITION WITH CONVERGENT FUNCTIONAL-GROUPS .6. SYNTHETIC AND STRUCTURAL STUDIES WITH A MODEL RECEPTOR FOR NUCLEIC-ACID COMPONENTS [J].

ASKEW, B ;

BALLESTER, P ;

BUHR, C ;

JEONG, KS ;

JONES, S ;

PARRIS, K ;

WILLIAMS, K ;

REBEK, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1082-1090

[4] New Kemp's diacid derivatives give efficient transport and modifiable selectivity for alkaline earth and transition metal ions [J].

Baldwin, BW ;

Hirose, T ;

Wang, ZH ;

Uchimaru, T ;

Yliniemela, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (08) :1895-1903

[5] ALLYLIC OXIDATIONS BY PEROXY ESTERS CATALYZED BY COPPER-SALTS - THE POTENTIAL FOR STEREOSELECTIVE SYNTHESES [J].

BECKWITH, ALJ ;

ZAVITSAS, AA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8230-8234

[6] Investigation of the effects of the structure and chelate size of bis-oxazoline ligands in the asymmetric copper-catalyzed cyclopropanation of olefins: Design of a new class of ligands [J].

Bedekar, AV ;

Koroleva, EB ;

Andersson, PG .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2518-2526

[7]

Bolm C, 1997, SYNLETT, P687

[8] BIS(4,5-DIHYDROOXAZOLYL) DERIVATIVES IN ASYMMETRIC CATALYSIS [J].

BOLM, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :542-543

[9] SYNTHESIS AND CRYSTAL-STRUCTURE OF A CHIRAL C-3-SYMMETRIC MONOPHOSPHANE [J].

BOLM, C ;

DAVIS, WM ;

HALTERMAN, RL ;

SHARPLESS, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :835-837

[10] SYNTHESIS OF A C3-SYMMETRIC PHOSPHA[2.2.2]CYCLOPHANE [J].

BOLM, C ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1988, 29 (40) :5101-5104

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