Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

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Abstract

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

Bibliographical metadata

Original languageEnglish
Pages (from-to)5570-5573
Number of pages4
JournalACS Catalysis
Volume8
Issue number6
Early online date14 May 2018
DOIs
Publication statusPublished - 1 Jun 2018