STEREOCONTROLLED SYNTHESES OF POLYSUBSTITUTED 2,3-DIHYDRO-4H-PYRAN-4-ONES BY CYCLOCONDENSATION OF BETA-ACYLOXY-KETONES

被引：22

作者：

OPPOLZER, W

RODRIGUEZ, I

机构：

[1] Département de Chimie Organique, Université de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1993年 / 76卷 / 03期

关键词：

D O I：

10.1002/hlca.19930760315

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

syn-beta-Acyloxy-ketones 6 and an anti-beta-acyloxy-ketone 17 undergo smooth intramolecular enolate/ester condensations 6 --> 18 and 17 --> 19 when treated with TiCl4/EtN(i-Pr)2. Thus, tri- and tetrasubstituted cis- or trans-2,3-dihydro-4H-pyran-4-ones are easily prepared in a stereoselective manner.

引用

收藏

页码：1282 / 1291

页数：10

相关论文

共 24 条

[1] LASIODERMA CHEMISTRY SEX-PHEROMONE OF CIGARETTE BEETLE (LASIODERMA-SERRICORNE F) [J].

CHUMAN, T ;

MOCHIZUKI, K ;

MORI, M ;

KOHNO, M ;

KATO, K ;

NOGUCHI, M .

JOURNAL OF CHEMICAL ECOLOGY, 1985, 11 (04) :417-434

[2] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[3] ON THE SCOPE OF ASYMMETRIC NITRILE OXIDE CYCLOADDITIONS WITH OPPOLZERS CHIRAL SULTAM - TOTAL SYNTHESES OF (+)-HEPIALONE, (-)-(1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE, AND (-)-(1S)-7,7-DIMETHYL-6,8-DIOXABICYCLO[3.2.1]OCTANE [J].

CURRAN, DP ;

HEFFNER, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4585-4595

[4]

Danishefsky S., 1989, CHEMTRACTS ORG CHEM, V2, P273

[5]

EBATA T, 1987, AGR BIOL CHEM TOKYO, V51, P2925

[6] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

[7] STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS [J].

EVANS, DA ;

RIEGER, DL ;

BILODEAU, MT ;

URPI, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1047-1049

[8] LEWIS ACID MEDIATED CONDENSATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF CHIRAL CARBAPENEM PRECURSORS [J].

FUENTES, LM ;

SHINKAI, I ;

SALZMANN, TN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4675-4676

[9] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS [J].

GAO, QZ ;

MARUYAMA, T ;

MOURI, M ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1951-1952

[10] ISOLATION AND STRUCTURE OF HEPIALONE - PRINCIPAL COMPONENT FROM MALE SEX SCALES OF HEPIALUS-CALIFORNICUS (LEPIDOPTERA) [J].

KUBO, I ;

MATSUMOTO, T ;

WAGNER, DL ;

SHOOLERY, JN .

TETRAHEDRON LETTERS, 1985, 26 (05) :563-566