Sj. Aitken et al., BIOHYDROXYLATIONS OF CBZ-PROTECTED ALKYL SUBSTITUTED PIPERIDINES BY BEAUVERIA-BASSIANA ATCC-7159, Journal of the Chemical Society. Perkin transactions. I (Print), (20), 1998, pp. 3365-3370
N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with
greater regioselectivity than the corresponding N-benzoyl analogues wh
en incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protect
ed piperidines 1-3, 5-7, have been biotransformed by growing cell susp
ensions of this fungus to yield predominantly 4-hydroxylated products
in up to 48% yield. The regiospecificity of hydroxylation was only com
promised significantly with N-Cbz-3-methylpiperidine 3 and N-Cbz-2-met
hylpiperidine 4 where hydroxylation occurred in both the 3 and 4 posit
ions.