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Asymmetric synthesis of 3-substituted cyclohexylamine derivatives from prochiral diketones via three biocatalytic steps

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Published copy (DOI)

Author(s)

  • E. Siirola
  • F.G. Mutti
  • B. Grischek
  • S.F. Hoefler
  • W.M.F. Fabian
  • W. Kroutil
  • G. Grogan

Department/unit(s)

Publication details

JournalAdvanced Synthesis and Catalysis
DatePublished - 17 Jun 2013
Issue number9
Volume355
Pages (from-to)1703-1708
Original languageEnglish

Abstract

Prochiral bicyclic diketones were transformed to a single diastereomer of 3-substituted cyclohexylamine derivatives via three consecutive biocatalytic steps. The two chiral centres were set up by a C-C hydrolase (6-oxocamphor hydrolase) in the first step and by an ω-transaminase in the last step. The esterification of the intermediate keto acid was catalysed by a lipase in the second step if possible. For two substrates the C-C hydrolytic step as well as the esterification could be run simultaneously in a one-pot cascade in an organic solvent. In one example, the reaction mixture of the first two steps could be directly subjected to bio-amination in an organic solvent without the need to change the reaction medium. Depending on the choice of the ω-transaminase employed and the substrate the cis- as well as the trans-diastereomers could be obtained in optically pure forms.

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