Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Dialkylammonium tert-Butylmethylphosphinites: Stable Intermediates for the Synthesis of P-Stereogenic Ligands

Dialkylammonium tert-Butylmethylphosphinites: Stable Intermediates for the Synthesis of P-Stereogenic Ligands
Xavier Verdaguer, Antoni Riera, Ernest Salomó, Amparo Prades
The preparation of shelf-stable crystalline salts of tert-butylmethylphosphinous acid borane 1 is described. X-ray analysis of diisopropylammonium tert-butylmethylphosphinite borane 6 revealed the presence of a cyclic hydrogen-bond network in the solid state which accounts for an increased melting point and stability. Dialkylammonium phosphinite boranes are convenient precursors of the chiral tert-butylmethylphosphine fragment. Compound 6 can be used directly in SN2@P reactions with various nucleophiles to yield valuable P-stereogenic intermediates and ligands.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01180

DOI: 10.1021/acs.joc.7b01180

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