Oxazolinyloxiranyllithium-mediated stereoselective synthesis of α-epoxy-β-amino acids

被引:29
作者
Luisi, R
Capriati, V
Degennaro, L
Florio, S
机构
[1] Univ Bari, Dipartimento Farmaco Chim, I-70126 Bari, Italy
[2] ICCOM, CNR, Bari, Italy
关键词
D O I
10.1021/ol034927q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective synthesis of novel alpha-epoxy-beta-amino acids is described by a route that combines the chemistry of oxazolinyloxiranyllithiums with that of nitrones. The intermediate trioxadiazadispiro[2.0.4.3]undecanes 4 have been isolated and converted by hydrolysis into epoxy-5-isoxazoildinones 5 which can be transformed into the alpha-epoxy-beta-amino acids 8 by N-O reduction.
引用
收藏
页码:2723 / 2726
页数:4
相关论文
共 26 条
[1]   A stereospecific synthesis of oxazolinyloxiranes [J].
Abbotto, A ;
Capriati, V ;
Degennaro, L ;
Florio, S ;
Luisi, R ;
Pierrot, M ;
Salomone, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3049-3058
[2]   Base-induced heterochiral dimerization of an oxiranyl carbaldimine:: Stereoselective synthesis of a highly functionalized aziridine [J].
Alickmann, D ;
Fröhlich, R ;
Wurthwein, EU .
ORGANIC LETTERS, 2001, 3 (10) :1527-1530
[3]  
Capriati V, 2001, EUR J ORG CHEM, V2001, P2035, DOI 10.1002/1099-0690(200106)2001:11<2035::AID-EJOC2035>3.0.CO
[4]  
2-R
[5]  
Capriati V, 2002, EUR J ORG CHEM, V2002, P2961, DOI 10.1002/1099-0690(200209)2002:17<2961::AID-EJOC2961>3.0.CO
[6]  
2-F
[7]   Oxiranyl anion-mediated synthesis of highly enantiomerically enriched styrene oxide derivatives [J].
Capriati, V ;
Florio, S ;
Luisi, R ;
Salomone, A .
ORGANIC LETTERS, 2002, 4 (14) :2445-2448
[8]  
COLE DC, 1994, TETRAHEDRON, V50, P9517
[9]  
Dechoux L, 2001, EUR J ORG CHEM, V2001, P4107
[10]   SYNTHESIS OF N-BENZYL NITRONES [J].
DONDONI, A ;
FRANCO, S ;
JUNQUERA, F ;
MERCHAN, F ;
MERINO, P ;
TEJERO, T .
SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2537-2550