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.
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页码：53 / 56
页数：4
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