Asymmetric hydrogenation of trisubstituted olefins with iridium-phosphine thiazole complexes: a further investigation of the ligand structure

Journal of the American Chemical Society
Christian HedbergPher G Andersson

Abstract

New chiral bidentate phoshine thiazoles have been prepared and successfully applied as ligands in the homogeneous iridium-catalyzed asymmetric hydrogenation of aryl alkenes and aryl alkene esters. The ligands are designed to be highly modular and have one common chiral intermediate, from which diversity can be introduced at a late stage in the synthetic pathway. It was found that a six-member-ring backbone of the rigid ligand structure was preferred over seven- or five-member rings. In this study it is shown that the substituent pattern of the ligands has a major influence on the stereochemical outcome of the products. By applying the selectivity model proposed in this study, it is possible to match different substrates against different catalysts. In this way, good to excellent enantioselectivity can be obtained for typically difficult substrates. Geometrically different derivatives of alpha- and beta-methyl cinnamic acid ethyl esters were hydrogenated, to demonstrate the validity of the selectivity model and to verify the importance of steric and electronic matching of the catalyst and the substrate.

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Citations

Feb 27, 2014·Chemical Reviews·J Johan VerendelPher G Andersson
Oct 8, 2009·Chemical Communications : Chem Comm·Alexander PaptchikhinePher G Andersson
Feb 18, 2011·Chemical Communications : Chem Comm·Alexander PaptchikhinePher G Andersson
May 11, 2011·Chemical Communications : Chem Comm·David H Woodmansee, Andreas Pfaltz
Jan 10, 2017·Journal of the American Chemical Society·Cristiana Margarita, Pher G Andersson
Oct 13, 2009·Bioorganic & Medicinal Chemistry Letters·Fernando R Pinacho CrisóstomoZiwei Huang
Feb 1, 2013·ACS Catalysis·Sakunchai Khumsubdee, Kevin Burgess
Jan 1, 2014·Chemistry, an Asian Journal·Quynh Nhu N Nguyen, Dean J Tantillo
Jun 22, 2007·Chemistry : a European Journal·Jianguang ZhouKevin Burgess
Jul 5, 2007·Angewandte Chemie·Jerome BayardonArmin Börner
Nov 29, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·J Johan Verendel, Pher G Andersson
Jul 12, 2008·Chemistry & Biodiversity·Alessandra CiappaUgo Matteoli
Apr 1, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Matthew S JeleticAdam S Veige
Dec 5, 2013·Chemical Communications : Chem Comm·Quanjun WangWeiping Chen
Apr 9, 2014·Angewandte Chemie·Maurizio BernasconiAndreas Pfaltz
Aug 15, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Alban Cadu, Pher G Andersson
Oct 23, 2016·Chemistry : a European Journal·Jingzhao XiaWanbin Zhang
Feb 2, 2011·Organic & Biomolecular Chemistry·Jeroen Wassenaar, Joost N H Reek
Apr 26, 2012·Chemistry : a European Journal·J Johan VerendelPher G Andersson
Jul 19, 2012·Chemistry : a European Journal·Jia-Qi LiPher G Andersson
Feb 1, 2014·Chemistry : a European Journal·Maurizio BernasconiAndreas Pfaltz
May 28, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Oscar PàmiesMontserrat Diéguez
Sep 13, 2012·Chemistry : a European Journal·David H WoodmanseeAndreas Pfaltz
Mar 29, 2008·Journal of the American Chemical Society·Pradeep CherukuPher G Andersson
Jun 19, 2010·Journal of the American Chemical Society·J Johan VerendelPher G Andersson
May 26, 2009·Journal of the American Chemical Society·Pradeep CherukuPher G Andersson
Oct 20, 2007·Chemical Reviews·Mohamed MellahEmmanuelle Schulz
Nov 18, 2010·Journal of the American Chemical Society·Stefan NaveVarinder K Aggarwal

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