dc.contributor.author | Rubina, Marina | |
dc.contributor.author | Sherrill, William M. | |
dc.contributor.author | Barkov, Alexey Yu | |
dc.contributor.author | Rubin, Michael | |
dc.date.accessioned | 2014-09-17T14:43:01Z | |
dc.date.available | 2014-09-17T14:43:01Z | |
dc.date.issued | 2014-07-07 | |
dc.identifier.citation | Marina Rubina, William M Sherrill, Alexey Yu Barkov, Michael Rubin "Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction" Beilstein J Org Chem. 2014; 10: 1536–1548. Published online 2014 July 7. http://dx.doi.org/10.3762/bjoc.10.158 | |
dc.identifier.uri | http://hdl.handle.net/1808/15017 | |
dc.description.abstract | A novel class of chiral phosphanyl-oxazoline (PHOX) ligands with a conformationally rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities and significantly suppressing product isomerization. Factors affecting the selectivity and the rate of the isomerization were identified. It was shown that the nature of this isomerization is different from that demonstrated previously using chiral diphosphine ligands. | |
dc.description.sponsorship | Financial support from the University of Kansas and the National Science Foundation (EEC-0310689) is gratefully acknowledged. We are grateful to International Collaboration Program, supported by the Ministry of Education and Science of the Russian Federation and the Ural Federal University. We also thank National Science Foundation (grant CHE-0079282) for funds to purchase the X-ray instrument and Dr. V. W. Day (X-ray Crystallography Laboratory, University of Kansas) for his assistance with X-ray crystallography. | |
dc.publisher | Beilstein-Institut | |
dc.subject | Asymmetric Catalysis | |
dc.subject | Chiral Phosphine Ligands | |
dc.subject | Cyclopropane | |
dc.subject | Heck Reaction | |
dc.subject | Organophosphorus | |
dc.subject | Transition Metal Catalysis | |
dc.title | Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction | |
dc.type | Article | |
kusw.kuauthor | Rubina, Marina | |
kusw.kuauthor | Sherrill, William M. | |
kusw.kuauthor | Rubin, Michael | |
kusw.kudepartment | Department of Chemistry | |
kusw.oastatus | fullparticipation | |
dc.identifier.doi | 10.3762/bjoc.10.158 | |
dc.identifier.orcid | https://orcid.org/0000-0002-1668-9311 | |
kusw.oaversion | Scholarly/refereed, publisher version | |
kusw.oapolicy | This item meets KU Open Access policy criteria. | |
dc.rights.accessrights | openAccess | |