Aldol-cyclization reaction sequence for the synthesis of tetrahydrofurans

被引：43

作者：

Calter, MA

Sugathapala, PM

Zhu, C

机构：

[1] Department of Chemistry, Virginia Tech., Blacksburg

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(97)00766-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol reactions of alpha-diazo-beta-ketoesters with a variety of aldehydes produced adducts which underwent Rh(II)-catalyzed O-H insertion reaction to yield highly substituted tetrahydrofurans. Alkylation and decarboxylation of these tetrahydrofurans formed a wide variety of tetrahydrofuran structures. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3837 / 3840

页数：4

相关论文

共 12 条

[1] NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .2. TOTAL SYNTHESIS OF 8-OXO-4-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACIDS [J].

BRYAN, DB ;

HALL, RF ;

HOLDEN, KG ;

HUFFMAN, WF ;

GLEASON, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) :2353-2355

[2] ERYTHRO-SELECTIVE ALDOL REACTION USING PHENYLDICHLOROBORANE [J].

HAMANA, H ;

SASAKURA, K ;

SUGASAWA, T .

CHEMISTRY LETTERS, 1984, (10) :1729-1732

[3]

Johnson A. W., 1973, ORG SYNTH, VV, P785

[4] DIAZO TRANSFER-REACTIONS UNDER MILDLY BASIC CONDITIONS [J].

KOSKINEN, AMP ;

MUNOZ, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (08) :652-653

[5] SYNTHETIC APPLICATIONS OF DEALKOXYCARBONYLATIONS OF MALONATE ESTERS, BETA-KETO-ESTERS, ALPHA-CYANO ESTERS AND RELATED-COMPOUNDS IN DIPOLAR APROTIC MEDIA .2. [J].

KRAPCHO, AP .

SYNTHESIS-STUTTGART, 1982, (11) :893-914

[6]

KRAPCHO AP, 1982, SYNTHESIS-STUTTGART, P805

[7] SYNTHESIS AND REACTIONS OF RING-A METHYLATED SATURATED STEROIDS [J].

MAZUR, Y ;

SONDHEIMER, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (19) :5220-5229

[8] INTRAMOLECULAR N-H, O-H, AND S-H INSERTION REACTIONS - SYNTHESIS OF HETEROCYCLES FROM ALPHA-DIAZO BETA-KETO-ESTERS [J].

MOYER, MP ;

FELDMAN, PL ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5223-5230

[9]

REIDER PJ, 1982, TETRAHEDRON LETT, V38, P379

[10] GENERAL-ROUTE TO HIGHLY FUNCTIONALIZED CYCLOPENTANE DERIVATIVES BY INTRAMOLECULAR C-H INSERTION [J].

TABER, DF ;

PETTY, EH .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4808-4809