CONCAVE WRAPPED PROTONS - REAGENTS FOR CONTRA-THERMODYNAMIC PROTONATIONS

被引:11
作者
LUNING, U
MULLER, M
机构
[1] Chemisches Laboratorium, Universität Freiburg, D-W-7800
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 01期
关键词
D O I
10.1002/anie.199200801
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Good stereoselectivity in the reprotonation of nitronate ions R2C--NO2 is achieved, if the bis-ortho-substituted 2-aryl-1, 10-phenanthroline 1 is added as a buffer. Both for cyclic and acyclic nitronate ions the reaction proceeds via transition states which lead to a thermodynamically less stable product. R = H, Me, Ph.
引用
收藏
页码:80 / 82
页数:3
相关论文
共 33 条
[1]   STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES [J].
ASHBY, EC ;
LAEMMLE, JT .
CHEMICAL REVIEWS, 1975, 75 (04) :521-546
[2]  
Barrett A. G. M., 1988, TETRAHEDRON LETT, V29, P5733
[3]  
COUTOIS G, 1974, J ORGANOMET CHEM, V69, P1
[5]   ENANTIOSELECTIVE ELECTROPHILIC BOND CONSTRUCTION TO THE ALPHA-CARBON OF ALPHA-AMINOACIDS [J].
DUHAMEL, L ;
DUHAMEL, P ;
FOUQUAY, S ;
EDDINE, J ;
PESCHARD, O ;
PLAQUEVENT, JC ;
RAVARD, A ;
SOLLIARD, R ;
VALNOT, JY ;
VINCENS, H .
TETRAHEDRON, 1988, 44 (17) :5495-5506
[7]  
Gerlach, 1987, ANGEW CHEM, V99, P1323
[8]   ENANTIOSELECTIVE PROTONATION OF CARBANIONS WITH CHIRAL PROTON SOURCES [J].
GERLACH, U ;
HUNIG, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1283-1285
[9]  
GIESE B, 1977, TETRAHEDRON LETT, P2783
[10]   THE STEREOSELECTIVITY OF INTERMOLECULAR FREE-RADICAL REACTIONS [J].
GIESE, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (08) :969-980