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Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)‐Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides
Author(s) -
Lee Seung Cheol,
Son JeongYu,
Kim Jin Young,
Eom Hyeonsik,
Jang Seong Bin,
Lee Phil Ho
Publication year - 2021
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.202001082
Subject(s) - chemistry , regioselectivity , azulene , rhodium , carbene , reactivity (psychology) , catalysis , surface modification , combinatorial chemistry , organic chemistry , alternative medicine , pathology , medicine
A regioselective and chemodivergent synthetic approach for azulenolactones and azulenolactams as a new scaffold was demonstrated through Rh(III)‐catalyzed reaction of N ‐methoxyazulene‐1‐carboxamides with sulfoxonium ylides. Sulfoxonium ylides that act as a precursor of secondary carbene was described, leading to the selective formation of azulenolactones and azulenolactams bearing two substituents on a newly introduced double bond. This method demonstrated functionalization of less reactive 2‐position of azulene to overcome the natural reactivity.