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Asymmetric Hydrogenation of Seven‐Membered C=N‐containing Heterocycles and Rationalization of the Enantioselectivity
Author(s) -
Balakrishna Bugga,
Bauzá Antonio,
Frontera Antonio,
VidalFerran Anton
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601464
Subject(s) - asymmetric hydrogenation , phosphine , enantioselective synthesis , chemistry , iridium , rationalization (economics) , catalysis , ligand (biochemistry) , stereochemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , philosophy , biochemistry , receptor , epistemology
Iridium(I) complexes with phosphine–phosphite ligands efficiently catalyze the enantioselective hydrogenation of diverse seven‐membered C=N‐containing heterocyclic compounds (eleven examples; up to 97 % ee ). The P‐OP ligand L3 , which incorporates an ortho ‐diphenyl substituted octahydrobinol phosphite fragment, provided the highest enantioselectivities in the hydrogenation of most of the heterocyclic compounds studied. The observed stereoselection was rationalized by means of DFT calculations.