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Cu II ‐Catalyzed Asymmetric Hydrosilylation of Diaryl‐ and Aryl Heteroaryl Ketones: Application in the Enantioselective Synthesis of Orphenadrine and Neobenodine
Author(s) -
Sui YaoZong,
Zhang XiChang,
Wu JunWen,
Li Shijun,
Zhou JiNing,
Li Min,
Fang Wenjun,
Chan Albert S. C.,
Wu Jing
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200379
Subject(s) - enantioselective synthesis , hydrosilylation , catalysis , aryl , chemistry , combinatorial chemistry , stoichiometry , copper , organic chemistry , alkyl
With certain amounts of sodium tert ‐butoxide and tert ‐butanol as additives, catalytic amounts of an inexpensive and easy‐to‐handle copper source Cu(OAc) 2 ⋅ H 2 O, a commercially available and air‐stable non‐racemic dipyridylphosphine ligand, as well as the stoichiometric desirable hydride donor polymethylhydrosiloxane (PMHS), formed a versatile in situ catalyst system for the enantioselective reduction of a broad spectrum of prochiral diaryl and aryl heteroarylketones in air, in high yields and with good to excellent enantioselectivities (up to 96 %). In particular, the practical viability of this process was evinced by its successful applications in the asymmetric synthesis of optically enriched potent antihistaminic drugs orphenadrine and neobenodine.