Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex

Journal of the American Chemical Society
Vincent S ChanF Dean Toste

Abstract

Ruthenium phosphido complexes have been shown to be excellent nucleophiles, reacting via two-electron processes with a variety of electrophiles. A catalytic alkylation reaction was developed using an achiral ruthenium complex, which was then elaborated into a catalytic enantioselective synthesis of P-stereogenic phosphines. These useful and synthetically challenging phosphines can now be accessed in a single step from simple secondary phosphines and alkyl halides. Optimization and scope of the enantioselective alkylation are discussed.

Citations

Apr 11, 2012·ACS Combinatorial Science·Magnus J JohanssonNina Kann
Oct 10, 2006·Chemical Communications : Chem Comm·Benoît JoinAnnie-Claude Gaumont
Sep 14, 2010·Chemical Communications : Chem Comm·James Stephen Harvey, Véronique Gouverneur
Sep 13, 2011·Chemical Communications : Chem Comm·Dan Du, Wei-Liang Duan
Jun 11, 2016·Journal of the American Chemical Society·Zhijian HuangYonggui Robin Chi
Mar 8, 2017·The Journal of Organic Chemistry·Hsin Y Su, Mark S Taylor
Feb 14, 2018·Science·Michael B Geeson, Christopher C Cummins
Aug 2, 2016·Chemical Society Reviews·Mathieu DutartreSylvain Jugé
Dec 28, 2017·Angewandte Chemie·Andrew M PoitrasChristine M Thomas
May 12, 2007·Angewandte Chemie·Ismail IbrahemArmando Córdova
May 21, 2008·Chemistry : a European Journal·David S Glueck
Oct 2, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·David S Glueck
Oct 28, 2010·Organic & Biomolecular Chemistry·Karla Bravo-AltamiranoJean-Luc Montchamp
Mar 30, 2007·Chemical Communications : Chem Comm·Giuseppe BartoliPaolo Melchiorre
Jul 19, 2019·Chemical Communications : Chem Comm·Raffael HuberAntonio Mezzetti
Jul 6, 2014·Beilstein Journal of Organic Chemistry·Iris WautersChristian V Stevens
Jan 30, 2020·Chemistry : a European Journal·Riccardo BonsignoreAngela Casini
Dec 17, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Rory Waterman
Sep 11, 2020·Chemical Communications : Chem Comm·Cuiying WangChi-Ming Che
Dec 14, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Shin TakemotoHiroyuki Matsuzaka
Oct 10, 2012·Chemical Communications : Chem Comm·Miao HuangSheng Xu
Mar 19, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tanuja TewariSamir H Chikkali
Apr 3, 2010·Journal of the American Chemical Society·Jian-Jun FengWei-Liang Duan
May 21, 2008·The Journal of Organic Chemistry·Magnus J JohanssonNina Kann
Nov 17, 2007·Journal of the American Chemical Society·Vincent S ChanF Dean Toste
Apr 10, 2021·Journal of the American Chemical Society·Chuanyong WangWei-Liang Duan
Feb 27, 2010·Organic Letters·James Stephen HarveyVéronique Gouverneur
Jun 24, 2021·Journal of the American Chemical Society·Shuai ZhangLiang Yin
Jul 21, 2021·Journal of the American Chemical Society·Xu-Teng LiuQing-Wei Zhang
Mar 14, 2007·Journal of Combinatorial Chemistry·Franck DolhemNina Kann
Jul 14, 2010·Inorganic Chemistry·Matthew F CainArnold L Rheingold
Aug 21, 2010·Inorganic Chemistry·Mitchell R AnsteyJoseph G Cordaro
Feb 13, 2014·Chemical Reviews·Jean-Pierre GenetVirginie Ratovelomanana-Vidal

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