Mechanistic aspects of asymmetric intramolecular Heck reaction involving dynamic kinetic resolution: flexible conformation of the cyclohexenylidene–benzene system. Issue 15 (15th April 2015)

• Record Type: Journal Article
• Authors: Hosoi, Shinzo; Ozeki, Minoru; Nakano, Masashi; Arimitsu, Kenji; Kajimoto, Tetsuya; Kojima, Naoto; Iwasaki, Hiroki; Miura, Takuya; Kimura, Hiroyuki; Node, Manabu; Yamashita, Masayuki
• Is Part Of: Tetrahedron. Volume 71:Issue 15(2015)
• Page Start: 2317
• Page End: 2326
• Publication Date: 2015-04-15
• Subjects: Intramolecular asymmetric Heck reaction -- Dynamic kinetic resolution -- Atropisomer; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.01.020
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An asymmetric intramolecular Heck reaction that involves the dynamic kinetic resolution of an atropisomer as the substrate furnished a product in high yield with high enantioselectivity. DFT calculations (Spartan'10, B3LYP/6-31G*) confirmed that the reaction proceeded via atropisomerization involving a conformational transformation (half-chair form/distorted-boat form) of the substrate. Graphical abstract: