Michael Blumenstein et.al.: Enantioselective Hydrogen Transfer from a Chiral
Tin Hydride to a Prochiral Carbon-Centered Radical
- Author(s): Michael Blumenstein,
Kay Schwarzkopf, Juergen O.
Metzger
- Title: Enantioselective Hydrogen Transfer from a Chiral Tin Hydride to
a Prochiral Carbon-Centered Radical
- Date of Upload: 1997
- Article: Angewandte Chemie, International Edition in English (1997),
36(3), 235-236, Department of Chemistry, University of Oldenburg,
Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany
- Keywords: asymmetric synthesis, homogenous catalysis, radicals,
tin, radical, reactions, selectivity, stereoselectivity, enantioselectivity
- Abstract:
- Chiral Sn hydrides (R)- and (S)-I were prepd. by successive treatment of
the corresponding 2,2'-bis(chloromethyl)-1,1'-binaphthyl with Me3CSnPhCl2, Br2
in MeOH, and LiAlH4 in Et2O. The structure of (R)-I, calcd. by MOPAC/PM3,
indicated possible capability of distinguishing between the enantiotopic faces
of a prochiral radical. Reducing Me3CCBrPhCO2Me with (R)-I at -78° gave 93%
Me3CCHPhCO2Me in 76:24 S/R ratio.
- URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/74_e.pdf
(application/pdf)
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