Premium
Gold(I)‐Catalyzed Intramolecular Hydroamination of N ‐Allylic N′ ‐Arylureas to form Imidazolidin‐2‐ones
Author(s) -
Li Hao,
Song Feijie,
Widenhoefer Ross A.
Publication year - 2011
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.201000844
Subject(s) - hydroamination , chemistry , allylic rearrangement , substituent , catalysis , medicinal chemistry , intramolecular force , yield (engineering) , hexafluorophosphate , organic chemistry , ionic liquid , materials science , metallurgy
Treatment of N ‐allylic N′‐ arylureas with a catalytic 1:1 mixture of di‐ tert ‐butyl‐ o ‐biphenylphoshphine gold(I) chloride and silver hexafluorophosphate (1 mol%) in chloroform at room temperature led to 5‐ exo ‐hydroamination to form the corresponding imidazolidin‐2‐ones in excellent yield. In the case of N ‐allylic ureas that possessed an allylic alkyl, benzyloxymethyl, or acetoxymethyl substituent, gold(I)‐catalyzed 5‐ exo ‐hydroamination leads to formation of the corresponding trans ‐3,4‐disubstituted imidazolidin‐2‐ones in excellent yield with ≥50:1 diastereoselectivity.