Rh2(S-1,2-NTTL)4: A Novel Rh2(S-PTTL)4 Analog With Lower Ligand Symmetry for Asymmetric Synthesis of Chiral Cyclopropylphosphonates

Frady Gouany, Ashraf GHANEM

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A new series of dirhodium(II) tetracarboxylate was derived from N-1,2-naphthaloyl-(S)-amino acid ligands. In terms of enantioselectivity, Rh2(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.

Original languageEnglish
Pages (from-to)764-774
Number of pages11
JournalChirality
Volume26
Issue number11
DOIs
Publication statusPublished - 2014

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Organophosphonates
Enantioselectivity
Amino acids
Ligands
Derivatives
Amino Acids
Catalysts
2-amino-3,3-dimethylbutanoic acid
dirhodium tetracarboxylate

Cite this

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title = "Rh2(S-1,2-NTTL)4: A Novel Rh2(S-PTTL)4 Analog With Lower Ligand Symmetry for Asymmetric Synthesis of Chiral Cyclopropylphosphonates",
abstract = "A new series of dirhodium(II) tetracarboxylate was derived from N-1,2-naphthaloyl-(S)-amino acid ligands. In terms of enantioselectivity, Rh2(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.",
keywords = "dirhodium, cyclopropanation, cyclopropylphosphonate, Rh2(S-PTAD)4, Rh2(S-NTTL)4, Rh2(S-PTTL)4, metal-carbenoids, paddlewheel-complexes",
author = "Frady Gouany and Ashraf GHANEM",
year = "2014",
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language = "English",
volume = "26",
pages = "764--774",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "11",

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Rh2(S-1,2-NTTL)4: A Novel Rh2(S-PTTL)4 Analog With Lower Ligand Symmetry for Asymmetric Synthesis of Chiral Cyclopropylphosphonates. / Gouany, Frady; GHANEM, Ashraf.

In: Chirality, Vol. 26, No. 11, 2014, p. 764-774.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Rh2(S-1,2-NTTL)4: A Novel Rh2(S-PTTL)4 Analog With Lower Ligand Symmetry for Asymmetric Synthesis of Chiral Cyclopropylphosphonates

AU - Gouany, Frady

AU - GHANEM, Ashraf

PY - 2014

Y1 - 2014

N2 - A new series of dirhodium(II) tetracarboxylate was derived from N-1,2-naphthaloyl-(S)-amino acid ligands. In terms of enantioselectivity, Rh2(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.

AB - A new series of dirhodium(II) tetracarboxylate was derived from N-1,2-naphthaloyl-(S)-amino acid ligands. In terms of enantioselectivity, Rh2(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.

KW - dirhodium

KW - cyclopropanation

KW - cyclopropylphosphonate

KW - Rh2(S-PTAD)4

KW - Rh2(S-NTTL)4

KW - Rh2(S-PTTL)4

KW - metal-carbenoids

KW - paddlewheel-complexes

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U2 - 10.1002/chir.22349

DO - 10.1002/chir.22349

M3 - Article

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JO - Chirality

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SN - 0899-0042

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