H-adamantylphosphinates as universal precursors of P-stereogenic compounds

J Org Chem. 2015 Apr 17;80(8):4132-41. doi: 10.1021/acs.joc.5b00548. Epub 2015 Apr 7.

Abstract

A new family of H-adamantylphosphinates as universal precursors of P-stereogenic ligands was obtained in one step from commercial chlorophosphines. Both enantiomers of these air- and moisture-stable intermediates can easily be separated by semipreparative chiral HPLC on a gram scale and individually undergo stereoselective transformations to afford each enantiomer of a set of P-stereogenic compounds such as secondary phosphine oxides and boron-protected monophosphines.