LIC-KOR promoted nitrone reactivity: stereoselective synthesis of highly conjugated imines and secondary amines

被引：3
|
作者：
Parisotto, Stefano [1 ]
Boggio, Paolo [1 ]
Prandi, Cristina [1 ]
Venturello, Paolo [1 ]
Deagostino, Annamaria [1 ]
机构：
[1] Univ Turin, Dept Chem, I-10125 Turin, Italy
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 42期
关键词：
LIC-KOR superbase; Alkoxydienes; Nitrones; Imines; Cyclopentenones; ALPHA; BETA-UNSATURATED ACETALS; NUCLEOPHILIC ADDITIONS; ORGANOLITHIUM COMPOUNDS; LITHIUM REAGENTS; CYCLOADDITIONS; METALATION; ROUTE;
D O I：
10.1016/j.tetlet.2015.08.087
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactivity of metalated alkoxy-1,3-dienes and alpha-aryl-N-phenylnitrones in the presence of LIC-KOR base, equimolar mixture of alkyllithium (LIC) and potassium alcoxides (KOR), (Schlosser, 1994) [1] has been studied. A cascade reaction involving a El cb process stereoselectively affords ethoxy-N-pheny1-1-arylpenta-2,4-dien-1-imines. Their acidic hydrolysis allows the synthesis of peptidomimetic 5-ary1-5-phenylaminocyclopentenones in good yields. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5791 / 5794
页数：4
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