Kai Schwarzkopf et.al.: Enantioselectivity of the Transfer of Hydrogen Atoms to Acyclic Prochiral Carbon-Centred Radicals Using Chiral Tin Hydrides

Author(s): Kai Schwarzkopf, Michael Blumenstein, Ahlke Hayen, Juergen O. Metzger

Title: Enantioselectivity of the Transfer of Hydrogen Atoms to Acyclic Prochiral Carbon-Centred Radicals Using Chiral Tin Hydrides

Date of Upload: 1998

Article: Eur. J. Org. Chem. 1998, 177-181, Department of Chemistry, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany

Keywords: Radicals, Chiral tin hydrides, Enantioselective radical reactions, Reductions, Radical reaction, selectivity, stereoselectivity, enantioselectivity

Abstract:
Racemic -bromo esters 2 have been reduced via prochiral radicals 5 with low to moderate enantioselectivities using chiral tin hydrides 1 with a stereogenic tin atom containing chiral 2-[(1-dimethylaminoalkyl)phenyl] ligands. The tin hydrides 1 were mixtures of diastereomers. It could be shown that the minor diastereomer of tin hydrides 1a and 1b reacts with good enantioselectivity whereas the major diastereomer reacts almost unselectively. The observed enantioselectivities are also strongly influenced by steric effects of the substituents attached to the radical centre.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/77.pdf (application/pdf)


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