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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