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.
Original language | English |
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Pages (from-to) | 5570-5573 |
Number of pages | 4 |
Journal | ACS Catalysis |
Volume | 8 |
Issue number | 6 |
Early online date | 14 May 2018 |
DOIs | |
Publication status | Published - 1 Jun 2018 |
Keywords
- alkaloidal tetrahydroquinoline
- amine oxidase
- biocatalysis
- enzymatic deracemization
- rhodium catalysis
Research Beacons, Institutes and Platforms
- Manchester Institute of Biotechnology