387819-51-4Relevant articles and documents
Chiral auxiliaries as docking/protecting groups: Biohydroxylation of selected ketones with Beauveria bassiana ATCC 7159
De Raadt, Anna,Fetz, Barbara,Griengl, Herfried,Florian Klingler, Markus,Krenn, Birgit,Mereiter, Kurt,Franz Münzer, Dieter,Plachota, Peter,Weber, Hansj?rg,Saf, Robert
, p. 8151 - 8157 (2007/10/03)
The concept of chiral docking/protecting groups for biohydroxylation was extended from cyclopentanone to other ketones. Reaction of cyclohexanone, (R)-3-methylcyclohexanone, cycloheptanone, 5-methyl-2-hexanone and 4-methyl-2-pentanone with (R)-2-amino-1-propanol and subsequent in situ benzoylation afforded the corresponding N-benzoylated oxazolidine derivatives. All substrates were hydroxylated with the fungus Beauveria bassiana ATCC 7159, one of which was diastereoselectively hydroxylated with a d.e. of 99%. In this manner, access to the corresponding hydroxylated ketones was provided.