PubMed: Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (-)-Cannabidiol

PubMed: Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (-)-Cannabidiol

Org Lett. 2024 Feb 15. doi: 10.1021/acs.orglett.3c04281. Online ahead of print.

ABSTRACT

The reaction of 4/5-carbonyl-cycloalkenone 1 or its achiral isomer 1′ with organoboronic acid 2 in the presence of a chiral diene (S,S)-Fc-tfb-rhodium catalyst gave disubstituted trans-cycloalkanone 3 with high diastereo- and enantioselectivity. This highly efficient dynamic kinetic resolution is achieved by fast racemization of 1 through the formation of a dienolate followed by kinetic resolution with the chiral catalyst. The utility is demonstrated by the synthesis of key intermediates en route to (-)-cannabidiol.

PMID:38358273 | DOI:10.1021/acs.orglett.3c04281

https://pubmed.ncbi.nlm.nih.gov/38358273/?utm_source=Chrome&utm_medium=rss&utm_campaign=pubmed-2&utm_content=1Ds1JEbG0OWaBdqM3tTUGjkFhFGaOtMecPdpuvzbuubWi6d9Fn&fc=20231022105433&ff=20240215132240&v=2.18.0 February 15, 2024 11:00 am