Concise asymmetric routes to 2,2,4-trisubstituted tetrahydrofurans via chiral titanium imide enolates: Key intermediates towards synthesis of highly active azole antifungals Sch 51048 and Sch 56592

被引：41

作者：

Saksena, AK ^{[1
]}

Girijavallabhan, VM ^{[1
]}

Wang, HY ^{[1
]}

Liu, YT ^{[1
]}

Pike, RE ^{[1
]}

Ganguly, AK ^{[1
]}

机构：

[1] SCHERING PLOUGH CORP,RES INST,KENILWORTH,NJ 07033

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 32期

关键词：

D O I：

10.1016/0040-4039(96)01203-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two complimentary approaches to the key (-)-(2R)-cis-tosylate 1 and its (+)-(2S)-enantiomer 15 via generation of chiral imide enolates having a 2,2-disubstituted olefin functionality in the P-position, are described. In a ''protecting group free'' sequence, reaction of the titanium enolate generated from (4R)-benzyl-2-oxazolidinone derived imide 5b with s-trioxane provided a convenient intermediate 19 which could be directly subjected to 2,4-diastereoselective iodocyclization. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：5657 / 5660

页数：4

共 9 条

[1]

[Anonymous], [No title captured]

[2] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].