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Gold‐Catalyzed Intermolecular anti‐Markovnikov Hydroamination of Methylenecyclopropanes with 2‐Pyridones
Author(s) -
Timmerman Jacob C.,
Widenhoefer Ross A.
Publication year - 2015
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.201500866
Subject(s) - hydroamination , chemistry , markovnikov's rule , phosphine , intermolecular force , cationic polymerization , catalysis , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , regioselectivity , molecule
The cationic gold phosphine complex [( o ‐biphenylPCy 2 )Au(NCMe)] + SbF 6 − catalyzes the intermolecular, anti‐Markovnikov hydroamination of methylenecyclopropanes (MCPs) with 2‐pyridones at 80 °C. The transformation was effective for a range of pyridones and for monosubstituted and cis ‐ and trans ‐disubstituted MCPs to form 1‐cyclopropylmethyl‐2‐pyridones with excellent regio‐ and diastereoselectivity in moderate to good yields.