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Transition‐Metal‐Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4‐Pyridones
Author(s) -
Schmidt Johannes P.,
Li Changkun,
Breit Bernhard
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701382
Subject(s) - stereoselectivity , chemistry , catalysis , enantioselective synthesis , transition metal , combinatorial chemistry , palladium , rhodium , stereochemistry , organic chemistry
A regiodivergent and stereoselective transition‐metal‐catalyzed addition of 4‐pyridones to allenes furnishing N ‐allylated pyridones is reported. Employing a commercially available chiral rhodium catalyst enabled enantioselective branched‐selective allylation. Conversely, an achiral palladium catalyst led to linear‐selective N ‐allylation in high E ‐selectivities. A wide range of functional groups was tolerated and assorted synthetic transformations of the N ‐allylated pyridones demonstrated their utility for the syntheses of medicinally relevant heterocyclic scaffolds.