Phosphorus-bearing axially chiral biaryls by catalytic asymmetric cross-cyclotrimerization and a first application in asymmetric hydrosilylation

Chemistry : a European Journal
Barbara HellerBernd Sundermann

Abstract

A novel and efficient, two-step route to axially chiral biaryls is demonstrated. In a direct asymmetric cross-cyclotrimerization in the presence of a chiral cobalt(I) catalyst, axially chiral biaryls bearing phosphoryl moieties have been prepared, and through indirect evidence the authors have been able to clarify the origin of the stereochemical induction and the nature of the central intermediate in the catalytic cycle. By subsequent reduction of the phosphoryl moiety to the corresponding phosphine, a very efficient and atom-economical approach to chiral systems has been developed. These chiral systems clearly have great potential use as axially chiral monodentate P- or bidentate P,O-ligands, as has been demonstrated by the employment of the novel NAPHEP as a new monodentate acting ligand in an asymmetric hydrosilylation reaction.

References

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Citations

Feb 11, 2016·Journal of the American Chemical Society·Christopher G NewtonNicolai Cramer
Sep 17, 2015·Journal of the American Chemical Society·David Kossler, Nicolai Cramer
Jan 27, 2017·Angewandte Chemie·Zhi-Jun JiaHerbert Waldmann
Nov 3, 2016·Angewandte Chemie·Barry M Trost, Michael C Ryan
May 21, 2008·Chemistry : a European Journal·David S Glueck
Jan 29, 2009·Angewandte Chemie·Anaïs GenyVincent Gandon
Jan 12, 2010·Chemistry, an Asian Journal·Azusa KondohKoichiro Oshima
Aug 4, 2015·Chemistry : a European Journal·Gaoyuan Ma, Mukund P Sibi
Oct 23, 2019·Nature Chemistry·Xiao-Yang DongXin-Yuan Liu
Jan 30, 2020·Chemistry : a European Journal·Tatsuhiko YoshinoShigeki Matsunaga
Mar 25, 2011·Chemical Society Reviews·Gema Domínguez, Javier Pérez-Castells
Apr 16, 2011·Chemistry : a European Journal·Jie HuShang-Dong Yang
Jan 27, 2011·Chemistry : a European Journal·Norifumi SakiyamaKen Tanaka
Jul 17, 2020·Angewandte Chemie·Josep Mas-RosellóNicolai Cramer
May 26, 2009·Journal of the American Chemical Society·Yuxing GaoLi-Biao Han
Jan 5, 2013·Journal of the American Chemical Society·Baihua Ye, Nicolai Cramer
Jan 12, 2013·Chemical Reviews·Anton V GulevichVladimir Gevorgyan
Jul 16, 2020·Journal of the American Chemical Society·Caitlin M B FarrSimon B Blakey

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