Raising the Ceiling of Diastereoselectivity in Hydrogen Transfer on Acyclic Radicals

I Denissova, L Maretti, BC Wilkes…

Index: Denissova, Irina; Maretti, Luca; Wilkes, Brian C.; Scaiano; Guindon, Yvan Journal of Organic Chemistry, 2009 , vol. 74, # 6 p. 2438 - 2446

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Citation Number: 7

Abstract

We report here that the monodentate complexation of Me2AlCl to an ester group significantly enhances the selectivity of hydrogen transfer on acyclic radicals flanked by both an ester functionality and a stereogenic center, leading to C-2, C-3-anti products with high diastereoselectivity. In certain cases improved ratios were obtained using bulkier aluminum Lewis acid such as MAD (methylaluminum-di (di-2, 6-tert-butyl-4-methylphenoxide). ...