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Aspects of stereocontrol in the L-Selectride reduction of 4-acyl-1,3-dioxolane derivatives

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Publication details

JournalTetrahedron
DateE-pub ahead of print - 4 Feb 2010
DatePublished (current) - 27 Mar 2010
Issue number13
Volume66
Number of pages10
Pages (from-to)2363-2372
Early online date4/02/10
Original languageEnglish

Abstract

The application of L-Selectride, either alone or in combination with ZnCl2, to aryl ketones 1, 8 and 11 resulted in highly anti-stereoselective reduction. In contrast, lactols 22 and 23 gave a moderate syn-preference using L-Selectride alone and a high syn-preference in the presence of ZnCl2. Uniquely, high anti- stereoselectivity was observed in the reduction of o-anisyl lactol 37 with L-Selectride alone, which was switched to a high syn-preference when ZnCl2 was present.

    Research areas

  • Diastereoselective, Ketones, Lactols, Polyols

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