CARBONYL ASSISTED INTRAMOLECULAR RING-OPENING OF 2-OXETANONES - A STEREOSELECTIVE ROUTE TO 2,5-DISUBSTITUTED TETRAHYDROFURANS

被引：16

作者：

MEAD, KT

PILLAI, SK

机构：

[1] Department of Chemistry, Mississippi State University Mississippi State

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 44期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)61580-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A carbonyl oxygen may serve as an internal nucleophile to open a 2-oxetanone ring by a beta-cleavage process. A sequence incorporating this strategy has been used to prepare 2,5-disubstituted tetrahydrofurans.

引用

页码：6997 / 7000

页数：4

共 8 条

[1] IODOETHERIFICATION OF HOMOALLYLIC ALCOHOLS - A STEREOSELECTIVE APPROACH TO TETRAHYDROFURANS [J].

BEDFORD, SB ;

BELL, KE ;

FENTON, G ;

HAYES, CJ ;

KNIGHT, DW ;

SHAW, D .

TETRAHEDRON LETTERS, 1992, 33 (43) :6511-6514

[2] TRIMETHYLSILYLKETENE - CYCLOADDITIONS OF KETENES AND ALDEHYDES [J].

BRADY, WT ;

SAIDI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) :733-737

[3] STEREOCHEMICAL CONTROL IN REACTIONS OF NUCLEOPHILES WITH OXOCARBENIUM IONS FORMED BY INTRAMOLECULAR OPENING OF ACTIVATED EPOXIDES BY NEIGHBORING CARBONYL GROUPS [J].

FOTSCH, CH ;

CHAMBERLIN, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4141-4147

[4] REAGENT-BASED STEREOCONTROL IN FORMATION OF SUBSTITUTED TETRAHYDROFURANS [J].

LIPSHUTZ, BH ;

BARTON, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :1084-1086

[5] SYNTHESIS AND INTRAMOLECULAR RING CLEAVAGE OF 2-OXETANONES [J].

MEAD, KT ;

SAMUEL, B .

TETRAHEDRON LETTERS, 1988, 29 (50) :6573-6576

[6] ERYTHRO SELECTIVE ADDITIONS OF TETRA-NORMAL-BUTYLAMMONIUM ENOLATES OF 2-OXETANONES TO ALDEHYDES - APPLICATION TO TETRAHYDROFURAN SYNTHESIS [J].

MEAD, KT ;

PARK, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2511-2514

[7] STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF 2,5-DISUBSTITUTED TETRAHYDROFURANS [J].

MULHOLLAND, RL ;

CHAMBERLIN, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1082-1085

[8] OXIDATIVE CYCLIZATION OF 5-HYDROXYALKENES WITH RHENIUM OXIDE, UTILIZING A COOXIDANT .4. [J].

TANG, SH ;

KENNEDY, RM .

TETRAHEDRON LETTERS, 1992, 33 (37) :5303-5306

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