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Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls
Author(s) -
Park Ga Eul,
Maezono Shizuka Mei Bautista,
Ha Ji Hyeon,
Shim JaeJin,
Kim Sung Hong,
Lee Yong Rok
Publication year - 2018
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.201800874
Subject(s) - chemistry , ketene , regioselectivity , intramolecular force , wolff rearrangement , carbene , nucleophile , cascade , nucleophilic addition , transition metal , cascade reaction , combinatorial chemistry , organic chemistry , catalysis , chromatography
An efficient protocol for the construction of 3‐carbonyl functionalized 4‐pyrones has been developed using a transition‐metal free thermal cascade reaction of diazodicarbonyls with β‐enamino esters or β‐enamino ketones. This reaction proceeds via cascade carbene generation, ketene formation via thermal Wolff‐rearrangement, nucleophilic addition, intramolecular cyclization, and elimination. This protocol provides a rapid synthetic route to diverse 2,3,5‐trisubstituted 4‐pyrone derivatives.