Michael reactions of titanium enolates of glycolic acid derivatives with the Weinreb and morpholine amides of acrylic acid

被引:19
作者
Olivella, Anna [1 ]
Rodriguez-Escrich, Carles [1 ]
Urpi, Felix [1 ]
Vilarrasa, Jaume [1 ]
机构
[1] Univ Barcelona, Fac Quim, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain
关键词
D O I
10.1021/jo702240n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The conjugate additions of titanium enolates of glycolate-derived chiral oxazolidin-2-ones to various Michael acceptors have been evaluated as an entry to enantiopure 1,2,5-trioxygenated and related synthons. alpha,beta-unsaturated Weinreb and morpholine amides do react under suitable conditions and their adducts can be converted to diverse C1-C5 chiral fragments.
引用
收藏
页码:1578 / 1581
页数:4
相关论文
共 32 条
[31]   STEREOSELECTIVE SYNTHESIS OF TRIFLUOROMETHYLATED COMPOUNDS WITH CONTROLLED ADJACENT TERTIARY CARBONS BY MICHAEL ADDITION TO (E)-3-(TRIFLUOROMETHYL)ACRYLATES [J].
SHINOHARA, N ;
HAGA, J ;
YAMAZAKI, T ;
KITAZUME, T ;
NAKAMURA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4363-4374
[32]   Strategy for enantio- and diastereoselective syntheses of all possible stereoisomers of 1,3-polyol arrays based on a highly catalyst-controlled epoxidation of α,β-unsaturated morpholinyl amides:: Application to natural product synthesis [J].
Tosaki, SY ;
Horiuchi, Y ;
Nemoto, T ;
Ohshima, T ;
Shibasaki, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (06) :1527-1544