Stereoselective synthesis of functionalized trans-2,5-disubstituted tetrahydrofurans

被引：31

作者：

Pilli, RA

Riatto, VB

Vencato, I

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

[2] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 01期

关键词：

D O I：

10.1021/ol991194u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The addition of the titanium enolates of N-acetyl, N-propionyl, and N-bromoacetyl (R)-oxazolidin-2-ones to gamma-lactol 2, derived from (S)-glutamic acid, afforded trans- and cis-2,5-disubstituted tetrahydrofurans (trans/cis ratio: R = H, 2:1; R = Me, 8:1; R = Br, 10:1) after desilylation with aqueous HF/CH3CN, Chromatographic separation and LiBH4 reduction allowed the efficient preparation of the corresponding trans-2,5-disubstituted tetrahydrofuran diols and the recovery of the chiral auxiliary.

引用

页码：53 / 56

页数：4

共 12 条

[1]

Ager DJ, 1996, SYNTHESIS-STUTTGART, P1283

[2]

BLACKWELL CM, 1992, J ORG CHEM, V57, P3887

[3] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].