One‐Pot Olefin Isomerization/Aliphatic Enamine Ring‐Closing Metathesis/Oxidation/1, 3‐Dipolar Cycloaddition for the Synthesis of Isoindolo[1, 2‐a]isoquinolines. Issue 18 (9th December 2015)

• Record Type: Journal Article
• Authors: Fujii, Yuki; Takehara, Tsunayoshi; Suzuki, Takeyuki; Fujioka, Hiromichi; Shuto, Satoshi; Arisawa, Mitsuhiro
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 18(2015)
• Page Start: 4055
• Page End: 4062
• Publication Date: 2015-12-09
• Subjects: cycloaddition -- domino reactions -- heterocycles -- metathesis -- ruthenium; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500680
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: N ‐Alkyl‐ N ‐(2‐vinylbenzyl)prop‐2‐en‐1‐amine derivatives undergo a one‐pot olefin isomerization/aliphatic enamine ring‐closing metathesis (RCM)/oxidation/1, 3‐dipolar cycloaddition sequence with the ruthenium complex, Ru(CO)HCl(PPh3 )3, a second generation Hoveyda–Grubbs catalyst, and a 1, 3‐dipolarophile. Overall, in a single operation the reaction sequence converts simple benzylamine derivatives into isoindolo[1, 2‐ a ]isoquinolines with a π‐conjugated four‐ring system, through three unique ruthenium‐catalyzed transformations. Abstract :