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 | Zendy

Adly Frady G. | Zendy; Maddalena Johncarlo | Zendy; Ghanem Ashraf | Zendy

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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.

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