Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 17, Pages 3729-3732Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000067
Keywords
annulation; aza-Michael; biocatalytic cascade; ketoynone; transaminase
Categories
Funding
- EPSRC
- EPSRC [EP/K014706/2, EP/K014668/1, EP/K014854/1, EP/K014714/1, EP/M013219/1]
- School of Chemistry UoN
Ask authors/readers for more resources
An omega-transaminase-triggered intramolecular aza-Michael reaction has been employed for the preparation of cyclic beta-enaminones in good yield and excellent enantio- and diastereoselectivity, starting from easily accessible prochiral ketoynones and commercially available enzymes. The powerful thermodynamic driving force associated with the spontaneous aza-Michael reaction effectively displaces the transaminase reaction equilibrium towards product formation, using only two equivalents of isopropylamine. To demonstrate the potential of this methodology, this biocatalytic aza-Michael step was combined with annulation chemistry, affording unique stereo-defined fused alkaloid architectures.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available