Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl)phenylphosphine oxide

Prochiral bis(cyanomethyl)phenylphosphine oxide has been successfully transformed into the corresponding optically active monoamide and monoacid with enantiomeric excesses ranging from low (15%) to very high (up to 99%) using a broad spectrum of nitrile-hydrolysing enzymes.

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CyanomethylphenylphosphinylacetamideC10H11N2O2PEe >99%[α]D = +7.2 (c 1, D2O + CD3COCD3)Source of chirality: enzymatic desymmetrisationAbsolute configuration: (S) (X-ray)

Cyanomethylphenylphosphinylacetic acidC10H10NO3PEe = 70%[α]D = −2.0 (c 1, D2O + CD3COCD3)Source of chirality: enzymatic desymmetrisationAbsolute configuration: (S) (comparative CD analysis)