Regio- and diastereoselective reduction of nonenolizable alpha-diketones to acyloins mediated by indium metal.
[reaction: see text] Alpha-diketones are efficiently reduced with indium metal in methanol-water in the presence of NH(4)Cl, LiCl, or NaCl to give regio- and diastereoselectively the corresponding acyloins in good to excellent yield. The cleavage of the acyloins under Pb(OAc)(4)/MeOH-PhH condition provides a convenient and regioselective access to highly functionalized cyclopentane carboxaldehydes, potential building blocks in organic syntheses.
Khan
Faiz Ahmed
FA
Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India. faiz@iitk.ac.in
Dash
Jyotirmayee
J
Sahu
Nilam
N
Gupta
Sharad
S