Journal
TETRAHEDRON
Volume 57, Issue 38, Pages 8151-8157Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00803-1
Keywords
Beauveria bassiana ATCC 7159; biohydroxylation; biotransformations; chiral auxiliaries; ketones
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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)-2amino-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. (C) 2001 Elsevier Science Ltd. All rights reserved.
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