Asymmetric Hydrogenation of Quinolines Catalyzed by Iridium Complexes of Monodentate BINOL-Derived Phosphoramidites

The monodentate BINOL‐derived phosphoramidite PipPhos is used as ligand for the iridium‐catalyzed asymmetric hydrogenation of 2‐ and 2,6‐substituted quinolines. If tri‐ortho‐tolylphosphine and/or chloride salts are used as additives enantioselectivities are strongly enhanced up to 89%. NMR indicates...

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Bibliographic Details
Published in:Advanced synthesis & catalysis Vol. 350; no. 7-8; pp. 1081 - 1089
Main Authors: Mršić, Nataša, Lefort, Laurent, Boogers, Jeroen A. F., Minnaard, Adriaan J., Feringa, Ben L., de Vries, Johannes G.
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 05.05.2008
WILEY‐VCH Verlag
Wiley
Subjects:
asymmetric hydrogenation
Chemistry
Chemistry, Applied
Chemistry, Organic
homogeneous catalysis
iridium
phosphoramidites
Physical Sciences
quinolines
Science & Technology
TRANSITION-METAL CATALYSIS
P-LIGANDS
ALLYLIC ALKYLATION
COMBINATORIAL APPROACH
HETEROAROMATIC-COMPOUNDS
ARYLBORONIC ACIDS
TROPOS PHOSPHORUS-LIGANDS
iridium
phosphoramidites
homogeneous catalysis
OLEFIN-HYDROGENATION
ENANTIOSELECTIVE TOTAL-SYNTHESIS
CONJUGATE ADDITIONS
asymmetric hydrogenation
quinolines
ISSN:1615-4150, 1615-4169
Online Access:Get full text
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Summary:The monodentate BINOL‐derived phosphoramidite PipPhos is used as ligand for the iridium‐catalyzed asymmetric hydrogenation of 2‐ and 2,6‐substituted quinolines. If tri‐ortho‐tolylphosphine and/or chloride salts are used as additives enantioselectivities are strongly enhanced up to 89%. NMR indicates that no mixed complexes are formed upon addition of tri‐ortho‐tolylphosphine.
Bibliography:ark:/67375/WNG-TBBLN8KZ-L
ArticleID:ADSC200800007
istex:BF483000650C96FEED2D1E0CB0FB7E95C38480F2
ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800007