Premium
Cooperative Organocatalysis: A Systematic Investigation of Covalently Linked Organophosphoric Acids for the Stereoselective Transfer Hydrogenation of Quinolines
Author(s) -
Thölke Simon,
Zhu Hui,
Jansen Dennis,
OctaSmolin Frescilia,
Thiele Maike,
Kaupmees Karl,
Leito Ivo,
Grimme Stefan,
Niemeyer Jochen
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900548
Subject(s) - chemistry , stereoselectivity , moiety , phosphoric acid , organocatalysis , organic chemistry , covalent bond , transfer hydrogenation , combinatorial chemistry , stereochemistry , enantioselective synthesis , catalysis , ruthenium
A series of covalently linked bis‐ and trisphosphoric acids was investigated for their application in the stereoselective transfer‐hydrogenation of quinolines. In a combined experimental and theoretical study, it was found that the number and relative positioning of the chiral 1,1′‐binaphthyl‐phosphoric acid groups strongly influences the stereoselectivity of the reaction, based on two competing reaction mechanisms. While a single 3‐monosubstituted phosphoric acid moiety gives rise to little enantioselectivity, correct positioning of two phosphoric acids allows a cooperative mechanism, resulting in significantly higher stereoselectivities.