Electron transfer induced stereoselective cyclization of 2,2-disubstituted dibenzoylmethane to anti-1,2-cyclopropanediol

DOI: 10.1016/00404-0399(50)1429L-

Source and publish data:

Tetrahedron Letters p. 6915 - 6918 (1995)

Update date:2022-08-04

Topics: Electron transfer NMR spectroscopy Catalyst Cyclization Stereoselective Chiral Resolution Reaction Conditions

Authors:

Hasegawa, Eietsu

Katagi, Hideyuki

Nakagawa, Daisuke

Horaguchi, Takaaki

Tanaka, Shyoji

Yamashita, Yoshiro

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Article abstract of DOI:10.1016/00404-0399(50)1429L-

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.

Full text of DOI:10.1016/00404-0399(50)1429L-

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