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Tandem Gold Self‐Relay Catalysis for the Synthesis of 2,3‐Dihydropyridin‐4(1 H )‐ones: Combination of σ and π Lewis Acid Properties of Gold Salts
Author(s) -
Fustero Santos,
Miró Javier,
SánchezRoselló María,
del Pozo Carlos
Publication year - 2014
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.201403340
Subject(s) - chemistry , tandem , trifluoromethanesulfonate , lewis acids and bases , salt (chemistry) , catalysis , intramolecular force , combinatorial chemistry , nucleophile , amide , lewis acid catalysis , cascade reaction , organic chemistry , medicinal chemistry , materials science , composite material
The dual ability of gold salts to act as π‐ and σ Lewis acids has been exploited in a tandem self‐relay catalysis. Thus, triphenylphosphanegold(I) triflate mediated the intramolecular carbonyl addition of the amide functionality of homoprogargyl amides to a triple bond. The formation of a σ complex of the gold salt with the intermediate oxazine promoted a nucleophilic addition followed by a Petasis–Ferrier rearrangement. This tandem protocol, catalyzed by the same gold salt under the same reaction conditions, gave rise to the efficient synthesis of 2,3‐dihydropyridin‐4‐(1 H )‐ones, which contain a cyclic quaternary α‐amino acid unit. The asymmetric version was performed by generating the starting materials from the corresponding sulfinylimines.