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A Gold‐Catalyzed Acid‐Assisted Regioselective Cyclization for the Synthesis of Polysubstituted Oxazoles
Author(s) -
Wang Qian,
Hoffmann Stephanie,
Schießl Jasmin,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900699
Subject(s) - regioselectivity , chemistry , oxazole , alkyne , catalysis , pyridine , combinatorial chemistry , organic chemistry
Polysubstituted oxazole derivatives are obtained through a regioselective gold‐catalyzed reaction of α‐alkynylamides and alkynoates in the presence of nitriles. The intermediary obtained gold carbenes are generated by alkyne oxidation with a pyridine N ‐oxide. Acidic conditions ensure that only one of the two carbonyl oxygen atoms in these intermediates selectively cyclizes to the products in excellent yields.