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Asymmetric hydrosilylation of prochiral ketones in the presence of N ‐benzyl‐ N ‐methylephedrinium halometallates
Author(s) -
Rubina K I,
Goldberg Yu Sh,
Shymanska M V,
Lukevics E
Publication year - 1987
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590010508
Subject(s) - hydrosilylation , chemistry , acetophenone , zincate , silyl ether , bromide , hydrolysis , medicinal chemistry , silylation , ether , benzyl bromide , yield (engineering) , organic chemistry , catalysis , materials science , zinc , metallurgy
N ‐benzyl‐ N ‐methylephedrinium hexachloroplatinate(IV), bromotrichlororhodate(III), and dibromodichlorozincate(II) have been synthesized by reacting (—)‐ N ‐benzyl‐ N ‐methylephedrinium bromide with K 2 PtCl 6 , RhCl 3 · 4H 2 O and ZnCl 2 , respectively. The above halometallates have been found to catalyse the asymmetric hydrosilylation of acetophenone and 3‐acetylpyridine with diphenylsilane. The hydrosilylation of 3‐acetylpyridine in the presence of (—)‐ N ‐benzyl‐ N ‐methylephedrinium zincate followed by silyl ether hydrolysis gives 1‐(3‐pyridyl)ethanol in ca 50% optical yield.