Michael Blumenstein et.al.: Enantioselective hydrogen transfer reactions from chiral binaphthyl variants of tin hydrides to prochiral radicals

Author(s): Michael Blumenstein, Matthias Lemmler, Ahlke Hayen, Jürgen O. Metzger

Title: Enantioselective hydrogen transfer reactions from chiral binaphthyl variants of tin hydrides to prochiral radicals

Date of Upload: 2003

Article: Tetrahedron : Asymmetry 14 (2003) 3069–3077, Department of Chemistry, University of Oldenburg, PO Box 2503, 26111 Oldenburg, Germany

Keywords: radical reactions, selectivity, stereoselectivity, enantioselectivity

Abstract:
Enantioselective, reagent-controlled radical reductions of prochiral alkyl radicals, mediated by binaphthyl variants oftin hydrides can be carried out in a highly selective fashion: a maximum selectivity of 68% e.e. was reached. Temperature, solvent, Lewis acid and substituent effects are selectivity-controlling elements. The reactions can be conducted catalytically with 1 mol% of chiral information and excess NaCNBH3.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/99.pdf (application/pdf)


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