Cu(II)-catalyzed asymmetric hydrosilylation of diaryl- and aryl heteroaryl ketones: application in the enantioselective synthesis of orphenadrine and neobenodine

Chemistry : a European Journal
Yao-Zong SuiJing Wu

Abstract

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.

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Feb 18, 2016·Chemical Reviews·Liang HongRui Wang
Mar 8, 2016·The Journal of Organic Chemistry·Hongxiang WuZhuo Zeng
Feb 26, 2015·Chemical Communications : Chem Comm·Ziqing ZuoZheng Huang
Aug 29, 2012·Chemistry, an Asian Journal·Fei-Fei WuJing Wu
Feb 12, 2020·Communications Chemistry·Jacob E DanderNeil K Garg
Jan 14, 2020·Bioorganic & Medicinal Chemistry Letters·Bini MathewMark J Suto
Aug 18, 2017·ACS Omega·Xiaochen MaZheng Huang
May 21, 2014·The Journal of Organic Chemistry·Manas Das, Donal F O'Shea

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