Abstract
The stereospecific hydrolysis of bulky aminophosphine boranes is reported for the first time. The resulting phosphinous acid boranes, upon activation, undergo stereospecific nucleophilic substitution reaction at the phosphorous center with amine nucleophiles. The combination of these two processes provides a novel access to bulky P*-ligands.
Highlights
The stereospecific hydrolysis of bulky aminophosphine boranes is reported for the first time
We recently reported the stereospecific synthesis of aminophosphines 1a and 1b which have been used by us in the preparation of MaxPHOS and SIP type ligands.[11]
We considered that these compounds were ideally suited to evaluate whether the acidolysis of bulky aminophosphines could be performed in a stereospecific manner, and whether the resulting products could be further transformed into valuable ligand structures (Scheme 1)
Summary
The stereospecific hydrolysis of bulky aminophosphine boranes is reported for the first time. The resulting phosphinous acid boranes, upon activation, undergo stereospecific nucleophilic substitution reaction at the phosphorous center with amine nucleophiles. Juge and others showed that P-stereogenic aryl and alkyl aminophosphine boranes undergo stereospecific acid-promoted methanolysis to yield the resulting methyl phosphinites with inversion a Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, E-08028, Spain.
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