Gualtieri, G and Geib, SJ and Curran, DP
(2003)
A new class of chiral organogermanes derived from C<inf>2</inf>-symmetric dithiols: Synthesis, characterization and stereoselective free radical reactions.
Journal of Organic Chemistry, 68 (13).
5013 - 5019.
ISSN 0022-3263
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Abstract
A new class of dithiostannanes and dithiogermanes have been prepared from 1,1′-binaphthyl-2,2′-dithiol and 3,3′-bis(trimethylsilyl)-1,1′ -binaphtho-2,2′-dithiol. While reduction of 4-butyl-4-chloro-3,5-dithia-4-stanna-cyclohepta[2,1-a;3,4- a′]dinaphthalene to the corresponding tin hydride was unsuccessful, 4-tert-butyl-3,5-dithia-4-germa-cyclohepta [2,1-a;3,4-a′]dinaphthalene and 4-tert-butyl- 2,6-bis(trimethylsilyl) -3,5-dithia-4-germa-cyclohepta[2,1-a;3,4-a′]dinaphthalene were obtained by reduction of the parent germanium chlorides with NaBH4 and LiBH4, respectively. Kinetic constants for hydrogen transfer to a primary alkyl radical were measured for both germanium hydrides. Reduction of α-halo carbonyl compounds by these germanium hydrides occurs with moderate ee values (up to 42%), while hydrogermylation of methyl methacrylate occurs with low selectivity (<3/1) for the former hydride but high selectivity (> 10/1) for the latter.
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