Copper(I) complexes of P-stereogenic Josiphos and related ligands

Ross A. Arthurs, Alice C. Dean, David L. Hughes, Christopher J. Richards

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Abstract

Starting from (R)-Ugi's amine, diastereoselective lithiation followed by Ar'PCl 2 and then Ar’’MgBr led to the generation, as single diastereoisomers, of (R,S p,S phos) [Ar’=Ph, Ar’’=o-Tol] and (R,S p,R phos) [Ar’=o-Tol, Ar’’=Ph] PPFA ligand derivatives. Amine substitution of both with HPCy 2 gave P-stereogenic Josiphos ligands, and then addition of CuCl, the corresponding copper(I) complexes. The latter were also generated by using borane P and N protecting groups and in situ Cu(I) complexation, avoiding the isolation of air-sensitive phosphine intermediates. This protection methodology was also applied to the synthesis of Josiphos/CuCl complexes derived from PCl 3. In addition, related bulky cobalt-sandwich complex-based derivatives were also obtained. Preliminary investigation revealed isolated CuCl complexes as competent catalyst precursors for enantioselective conjugate addition reactions.

Original languageEnglish
Pages (from-to)2719-2725
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number18
Early online date14 Apr 2021
DOIs
Publication statusPublished - 14 May 2021

Keywords

  • Asymmetric Catalysis
  • Copper
  • Ligand design
  • Metallocene
  • Protecting groups

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