jo5b00102_si_005.cif (15.71 kB)
Intermolecular Reductive Coupling of Esters with Benzophenones by Low-Valent Titanium: Synthesis of Diarylmethyl Ketones Revisited
dataset
posted on 2015-04-03, 00:00 authored by Naoki Kise, Toshihiko SakuraiThe reductive coupling of aliphatic
esters with benzophenones by
Zn–TiCl4 in THF gave two- and four-electron reduced
products, diaryl(hydroxy)methyl ketones, and diarylmethyl ketones
selectively by controlling the reaction conditions. In the reaction
of aromatic esters with benzophenones, diarylmethyl ketones were obtained
as the sole products. N-(Alkoxycarbonyl)-(S)-α-amino acid methyl esters gave optically active
diphenylmethyl ketones by reduction with benzophenone. The obtained
diphenylmethyl ketones were transformed to 4,5-cis-disubstituted oxazolidin-2-ones stereoselectively.