Tetrahedron Letters p. 6915 - 6918 (1995)
Update date:2022-08-04
Topics: Electron transfer NMR spectroscopy Catalyst Cyclization Stereoselective Chiral Resolution Reaction Conditions 2,2-disubstituted dibenzoylmethane Anti-1,2-cyclopropanediol
Hasegawa, Eietsu
Katagi, Hideyuki
Nakagawa, Daisuke
Horaguchi, Takaaki
Tanaka, Shyoji
Yamashita, Yoshiro
Irradiation of 2,2-dimethyl-1,3-diphenyl-1,3-propanedione in the presence of triethylamine gave anti-2,2-dimethyl-1,3-diphenyl-1,3-cyclopropanediol as a major product. On the basis of the results obtained, the mechanism involving single electron transfer between the excited diketone and the ground state amine followed by the anion radical rearrangement was proposed. The same cyclized product was also obtained for the reaction with samarium diiodide.
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