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Enantioselective Synthesis of a Novel Chiral 2,9‐Disubstituted 1,10‐Phenanthroline and First Applications in Asymmetric Catalysis
Author(s) -
Nandakumar Mecheril Valsan,
Ghosh Subrata,
Schneider Christoph
Publication year - 2009
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.200901038
Subject(s) - enantioselective synthesis , chemistry , phenanthroline , catalysis , stereoselectivity , pyridine , ligand (biochemistry) , combinatorial chemistry , asymmetric carbon , ring (chemistry) , stereochemistry , organic chemistry , optically active , receptor , biochemistry
The asymmetric synthesis of a novel, C 2 ‐symmetric, tetradentate 1,10‐phenanthroline is described; it is based on the stereoselective preparation of two functionalized pyridine subunits, which were subsequently joined through two consecutive carbon–carbon bond‐forming reactions to assemble the heteroaromatic system. Some initial applications of this new chiral ligand in metal‐catalyzed, enantioselective ring‐opening reactions of meso ‐epoxides and aminations of β‐keto esters are presented.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)