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
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共 32 条
[21]  
Martin R, 1997, SYNLETT, P1414
[22]   Synthetic routes to the stereoisomers of 2,4-dimethylpentane-1,5-diol derivatives [J].
Mas, G ;
González, L ;
Vilarrasa, J .
TETRAHEDRON LETTERS, 2003, 44 (49) :8805-8809
[23]  
MAS G, 2000, THESIS U BARCELONA
[24]  
MIYAZAKI T, 2004, ALDRICHIM ACTA, V37, P87
[25]   N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].
NAHM, S ;
WEINREB, SM .
TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818
[26]   IMPROVED PROCEDURE FOR THE REDUCTION OF N-ACYLOXAZOLIDINONES [J].
PENNING, TD ;
DJURIC, SW ;
HAACK, RA ;
KALISH, VJ ;
MIYASHIRO, JM ;
ROWELL, BW ;
YU, SS .
SYNTHETIC COMMUNICATIONS, 1990, 20 (02) :307-312
[27]   A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones from N-acyloxazolidinones with sodium borohydride [J].
Prashad, M ;
Har, D ;
Kim, HY ;
Repic, O .
TETRAHEDRON LETTERS, 1998, 39 (39) :7067-7070
[28]   Toward a total synthesis of amphidinolide X and Y.: The tetrahydrofuran-containing fragment C12-C21 [J].
Rodriguez-Escrich, Carles ;
Olivella, Anna ;
Urpi, Felix ;
Vilarrasa, Jaume .
ORGANIC LETTERS, 2007, 9 (06) :989-992
[29]   An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation [J].
Ruiz, J ;
Ardeo, A ;
Ignacio, R ;
Sotomayor, N ;
Lete, E .
TETRAHEDRON, 2005, 61 (13) :3311-3324
[30]   Amino acid derived morpholine amides for nucleophilic α-amino acylation reactions:: A new synthetic route to enantiopure α-amino ketones [J].
Sengupta, S ;
Mondal, S ;
Das, D .
TETRAHEDRON LETTERS, 1999, 40 (21) :4107-4110