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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