Chiral auxiliaries as docking/protecting groups: biohydroxylation of selected ketones with Beauveria bassiana ATCC 7159

The concept of chiral docking/protecting groups for biohydroxylation was ex tended from cyclopentanone to other ketones. Reaction of cyclohexanone, (R) -3-methylcyclohexanone, cycloheptanone, 5-methyl-2-hexanone and 4-methyl-2- pentanone with (R)-2amino-1-propanol and subsequent in situ benzoylation af forded the corresponding N-benzoylated oxazolidine derivatives. All substra tes were hydroxylated with the fungus Beauveria bassiana ATCC 7159, one of which was diastereoselectively hydroxylated with a d.e. of 99%. In this man ner, access to the corresponding hydroxylated ketones was provided. (C) 200 1 Elsevier Science Ltd. All rights reserved.