U. Lindemann et al., Photoinduced diastereoselective pinacolisation of 4-oxo-4-phenylbutanamides to 4,5-dihydroxy-4,5-diphenyloctanediamides, J CHEM S P2, (10), 1999, pp. 2029-2036
Citations number
28
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
The photoinduced pinacolisation of 4-oxo-4-phenylbutanamides 1 afforded 4,5
-dihydroxy-4,5-diphenyloctanediamides 2 and 3 with unusual diastereoselecti
vities up to 83%, which depends on the amide substituent. In this reaction
the solvent diethyl ether acts as a hydrogen donor. The structures of pinac
ols 2 and 3 were confirmed by X-ray analyses. Possible reasons for the dias
tereoselectivity and the preferred intermolecular hydrogen abstraction from
the solvent are discussed. Products 5 and 6 obtained after irradiation of
4-oxo-4-phenylbutanoic acid 4 were identified by crystal structure determin
ation as 2,2'-diphenyltetrahydro[2,2']bifuranyl-5,5'-diones.