Enantioselective synthesis of planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites and their use as chiral ligands

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Abstract

A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained.

Original languageEnglish
Pages (from-to)1081-1087
Number of pages7
JournalTetrahedron Asymmetry
Volume27
Issue number20-21
DOIs
Publication statusPublished - 2016 Nov 15

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Amination
Enantioselectivity
alkylation
Alkylation
seats
Ligands
Chalcone
ligands
synthesis
phosphoramidite
methyl malonate

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

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title = "Enantioselective synthesis of planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites and their use as chiral ligands",
abstract = "A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained.",
author = "Madhurima Hazra and Kanyiva, {Stephen Kyalo} and Takanori Shibata",
year = "2016",
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language = "English",
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T1 - Enantioselective synthesis of planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites and their use as chiral ligands

AU - Hazra, Madhurima

AU - Kanyiva, Stephen Kyalo

AU - Shibata, Takanori

PY - 2016/11/15

Y1 - 2016/11/15

N2 - A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained.

AB - A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained.

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