Cargando…

Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes

The previously reported concept of using mixtures of monodentate ligands in a combinatorial manner in order to influence enantio- or regioselectivity of transition metal catalyzed processes has been extended to include diastereoselectivity. Accordingly, 1,2- and 1,3-asymmetric induction in the Rh-ca...

Descripción completa

Detalles Bibliográficos
Autores principales: Reetz, Manfred T, Guo, Hongchao
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2005
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399451/
https://www.ncbi.nlm.nih.gov/pubmed/16542016
http://dx.doi.org/10.1186/1860-5397-1-3
_version_ 1782126987448418304
author Reetz, Manfred T
Guo, Hongchao
author_facet Reetz, Manfred T
Guo, Hongchao
author_sort Reetz, Manfred T
collection PubMed
description The previously reported concept of using mixtures of monodentate ligands in a combinatorial manner in order to influence enantio- or regioselectivity of transition metal catalyzed processes has been extended to include diastereoselectivity. Accordingly, 1,2- and 1,3-asymmetric induction in the Rh-catalyzed hydrogenation of a chiral allylic alcohol and a chiral homo-allylic alcohol has been studied by using mixtures of monodentate P-ligands. It was found that appropriate 1:1 mixtures of two different P-ligands enhance the degree of diastereoselectivity relative to the use of the respective pure ligands themselves. Here, as in the previous cases regarding enantio- or regioselectivity, this type of combinatorial catalysis leads to improved catalytic profiles without the need to prepare new ligands.
format Text
id pubmed-1399451
institution National Center for Biotechnology Information
language English
publishDate 2005
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-13994512006-03-13 Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes Reetz, Manfred T Guo, Hongchao Beilstein J Org Chem Preliminary Communication The previously reported concept of using mixtures of monodentate ligands in a combinatorial manner in order to influence enantio- or regioselectivity of transition metal catalyzed processes has been extended to include diastereoselectivity. Accordingly, 1,2- and 1,3-asymmetric induction in the Rh-catalyzed hydrogenation of a chiral allylic alcohol and a chiral homo-allylic alcohol has been studied by using mixtures of monodentate P-ligands. It was found that appropriate 1:1 mixtures of two different P-ligands enhance the degree of diastereoselectivity relative to the use of the respective pure ligands themselves. Here, as in the previous cases regarding enantio- or regioselectivity, this type of combinatorial catalysis leads to improved catalytic profiles without the need to prepare new ligands. Beilstein-Institut 2005-08-26 /pmc/articles/PMC1399451/ /pubmed/16542016 http://dx.doi.org/10.1186/1860-5397-1-3 Text en Copyright © 2005, Reetz and Guo https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Reetz, Manfred T
Guo, Hongchao
Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes
title Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes
title_full Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes
title_fullStr Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes
title_full_unstemmed Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes
title_short Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes
title_sort mixtures of monodentate p-ligands as a means to control the diastereoselectivity in rh-catalyzed hydrogenation of chiral alkenes
topic Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399451/
https://www.ncbi.nlm.nih.gov/pubmed/16542016
http://dx.doi.org/10.1186/1860-5397-1-3
work_keys_str_mv AT reetzmanfredt mixturesofmonodentatepligandsasameanstocontrolthediastereoselectivityinrhcatalyzedhydrogenationofchiralalkenes
AT guohongchao mixturesofmonodentatepligandsasameanstocontrolthediastereoselectivityinrhcatalyzedhydrogenationofchiralalkenes