Enzymatic kinetic resolution in the synthesis of new precursors of P-chiral organophosphorus catalysts: phosphines and their P-boranes

Abstract

The CAL-B-mediated kinetic resolution of racemic 2-hydroxymethylphenyl-(methyl)phenylphosphine and its P-BH₃ analogue gave, via their enantioselective monoacetylation, the corresponding monoacetates and unreacted substrates in moderate yields and with indeterminate enantiomeric excess, depending on the solvent applied. The P-BH₃ analogues were transformed into 2-aminomethyl derivatives via O-tosyl or O-mesyl intermediates, which will be checked as tridentate catalyst/ligands in asymmetric synthesis.

Graphical Abstract

Keywords:

• Kinetic resolution
• acetylation
• phosphine
• phosphine P-borane

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

Financial support by the National Research Centre (NCN), Poland, grant PRELUDIUM: UMO-2014/13/N/ST5/03481 for L. M., is gratefully acknowledged.