The diverse chemistry of oxazol-5-(4H)-ones

被引:266
作者
Fisk, Jason S.
Mosey, Robert A.
Tepe, Jetze J. [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
[2] Saginaw Valley State Univ, Saginaw, MI USA
[3] Michigan State Univ, E Lansing, MI 48824 USA
[4] No Michigan Univ, E Lansing, MI USA
[5] Univ Virginia, Charlottesville, VA 22903 USA
关键词
D O I
10.1039/b511113g
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
The assembly of structurally diverse scaffolds via substrate controlled diversity oriented synthesis ( DOS) has proven to be an effective tool in the discovery of novel biologically important compounds. This tutorial review aims to summarize some of the more recent applications of oxazolones as a general template for the stereoselective syntheses of amino acids and heterocyclic scaffolds. A brief introduction covers a short history, nomenclature and general reactivity of oxazolones. The main body of this tutorial review highlights several applications of oxazolones as starting blocks for the diverse and stereoselective synthesis of amino acids, oxazoles, beta-lactams, pyrroles, imidazolines, pyrrolines, and imidazoles.
引用
收藏
页码:1432 / 1440
页数:9
相关论文
共 40 条
[1]
[Anonymous], 1960, J AM CHEM SOC, V82, P5545
[2]
Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones [J].
Berkessel, A ;
Mukherjee, S ;
Cleemann, F ;
Müller, TN ;
Lex, J .
CHEMICAL COMMUNICATIONS, 2005, (14) :1898-1900
[3]
Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core [J].
Bilodeau, MT ;
Cunningham, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2800-2801
[4]
Dynamic kinetic resolution:: synthesis of optically active α-amino acid derivatives [J].
Brown, SA ;
Parker, MC ;
Turner, NJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1687-1690
[5]
1.3-DIPOLAR CYCLOADDITIONS .61. CYCLOADDITIONS OF N-SUBSTITUTED OXAZOLIUM-5-OLATES TO NITRILES, NITRO, NITROSO AND AZO COMPOUNDS [J].
BRUNN, E ;
FUNKE, E ;
GOTTHARD.H ;
HUISGEN, R .
CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (05) :1562-&
[6]
CLARKE HT, 1949, OXAZOLES OXAZOLONES, P688
[7]
5(4H)-oxazolones.: Part XI.: Cycloaddition reaction of oxazolones and munchnones to triphenylvinylphosphonium salts as synthetic equivalents of alkynes. [J].
Clerici, F ;
Gelmi, ML ;
Trimarco, P .
TETRAHEDRON, 1998, 54 (21) :5763-5774
[8]
CONSONNI R, 1991, J CHEM RES-S, P188
[9]
[2+2] Cycloaddition reactions of imines with cyclic ketenes:: Synthesis of 1,3-thiazolidine derived spiro-β-lactams and their transformations [J].
Cremonesi, G ;
Dalla Croce, P ;
La Rosa, C .
HELVETICA CHIMICA ACTA, 2005, 88 (06) :1580-1588
[10]
ENZYMATIC ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ENANTIOSELECTIVE CLEAVAGE OF 4-SUBSTITUTED OXAZOLIN-5-ONES AND THIAZOLIN-5-ONES [J].
CRICH, JZ ;
BRIEVA, R ;
MARQUART, P ;
GU, RL ;
FLEMMING, S ;
SIH, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3252-3258