络合作用促进了对N-苯甲酰基亚氨基吡啶叶立德的加成反应。一种合成多取代哌啶的新颖且高度区域选择性的方法。
Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines.
作者信息
Legault Claude, Charette André B
机构信息
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada.
出版信息
J Am Chem Soc. 2003 May 28;125(21):6360-1. doi: 10.1021/ja0348647.
PMID:12785763
Abstract
Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.
摘要
在将不同的有机金属亲核试剂加成到N-苯甲酰基亚氨基吡啶叶立德上时，观察到了前所未有的区域选择性。即使是通常会生成大量1,4-加成物的苄基和支链脂肪族格氏试剂，也表现出优异的1,2-区域选择性。考虑了吡啶叶立德的电子性质来解释这些结果。
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