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Anionic Reactions of N ‐( trans ‐2,3‐Diphenylaziridin‐1‐yl)imines and Their Use as 1,1‐Dipoles in Anionic Cyclizations
Author(s) -
Hwang Jungll,
Hong YoungTaek,
Kim Sunggak
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505110
Subject(s) - chemistry , medicinal chemistry , imine , nitrogen , organic chemistry , catalysis
Reaction of N ‐( trans ‐2,3‐diphenylaziridin‐1‐yl)imines with alkyllithiums and organocuprates afforded the desired addition products after consecutive fragmentations along with liberation of stilbene and nitrogen gas, while the reaction of N ‐(2‐phenylaziridin‐1‐yl)imines under similar conditions gave an anomalous by‐product. Anionic cyclizations of N ‐( trans ‐2,3‐diphenylaziridin‐1‐yl)imines using unactivated alkenes and alkynes as acceptors proceeded smoothly, yielding cyclized products in good yields.