Regio- and diastereoselective reduction of nonenolizable alpha-diketones to acyloins mediated by indium metal |
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| Authors: | Khan Faiz Ahmed Dash Jyotirmayee Sahu Nilam Gupta Sharad |
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| Affiliation: | Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India. faiz@iitk.ac.in |
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| Abstract: | [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. |
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