Intermolecular reductive coupling of esters with benzophenones by low-valent titanium: synthesis of diarylmethyl ketones revisited

The Journal of Organic Chemistry
Naoki Kise, Toshihiko Sakurai

Abstract

The 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.

References

Dec 20, 2003·Organic Letters·Edward L Clennan, Gui-lan Pan
Nov 5, 2005·The Journal of Organic Chemistry·Naoki KiseNasuo Ueda
May 22, 2009·Organic Letters·Jason R Schmink, Nicholas E Leadbeater
Mar 2, 2010·Journal of the American Chemical Society·Yichen Tan, John F Hartwig
Mar 20, 2010·Organic Letters·Austin G Smith, Jeffrey S Johnson
Oct 13, 2012·Organic Letters·Yan-ping ZhuAn-xin Wu
May 21, 2013·Organic Letters·Naoki KiseToshihiko Sakurai
Jan 24, 2014·Angewandte Chemie·Vaibhav P MehtaMichael F Greaney

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Citations

Nov 22, 2017·The Journal of Organic Chemistry·Michelle A KrocLaura L Anderson

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