Anti-selective aldol reactions with titanium enolates of N-glycolyloxazolidinethiones

被引：82

作者：

Crimmins, MT ^{[1
]}

McDougall, PJ ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol034001i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly diastereoselective anti aldol addition utilizing a variety of N-glycolyloxazolidinethiones has been developed. Enolization of an N-glycolyloxazolidinethione with titanium (IV) chloride and (-)-sparteine followed by addition of an aldehyde activated with additional TiCl4 resulted in highly anti-selective aldol additions, typically with no observable syn isomers. Allyl-protected glycolates demonstrated the highest levels of selection and yields, although O-benzyl and O-methyl glycolyloxazolidinethiones also performed well.

引用

页码：591 / 594

页数：4

共 15 条

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