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Rh 2 ( S ‐1,2‐NTTL) 4 : A Novel Rh 2 ( S ‐PTTL) 4 Analog With Lower Ligand Symmetry for Asymmetric Synthesis of Chiral Cyclopropylphosphonates
Author(s) -
Adly Frady G.,
Maddalena Johncarlo,
Ghanem Ashraf
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22349
Subject(s) - chemistry , phosphonate , enantioselective synthesis , enantiomer , chirality (physics) , ligand (biochemistry) , rhodium , stereochemistry , catalysis , medicinal chemistry , organic chemistry , symmetry breaking , chiral symmetry breaking , receptor , biochemistry , physics , quantum mechanics , nambu–jona lasinio model
A new series of dirhodium(II) tetracarboxylate was derived from N ‐1,2‐naphthaloyl‐( S )‐amino acid ligands. In terms of enantioselectivity , Rh 2 ( S ‐1,2‐NTTL) 4 ( 3a ) derived from N ‐1,2‐naphthaloyl‐( S )‐ tert ‐leucine, was the best‐performing catalyst among the new series in the enantioselective synthesis of cyclopropylphosphonate derivatives (up to >99% enantiomeric excess). A predictive model was proposed to justify the observed high enantiomeric induction exhibited by Rh 2 ( S ‐1,2‐NTTL) 4 with donor‐acceptor phosphonate carbenoids. Chirality 26:764–774, 2014 . © 2014 Wiley Periodicals, Inc.