Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)‐Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides. Issue 2 (18th November 2020)

• Record Type: Journal Article
• Authors: Lee, Seung Cheol; Son, Jeong‐Yu; Kim, Jin Young; Eom, Hyeonsik; Jang, Seong Bin; Lee, Phil Ho
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 2(2021)
• Page Start: 512
• Page End: 524
• Publication Date: 2020-11-18
• Subjects: azulene -- rhodium -- azulenolactone -- azulenolactam -- sulfoxonium ylide; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202001082
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :