Rh(I)-catalyzed enantioselective (3 + 2) transannulations of 1,2,3-thiadiazoles with P-chiral monodentate phosphines

Abstract

As a proof of concept, P-chiral monodentate phosphines, which were inactive in promoting the transannulations of 1,2,3-thiadiazoles, were proven viable in the asymmetric catalytic (3 + 2) transannulations of 1,2,3-thiadiazoles with a strained bicyclic alkene. Polycyclic dihydrothiophenes with four newly formed stereocenters are generated in moderate 19-72% yields and 11-27% enantiopurities.

Graphical Abstract

Keywords:

• Asymmetric catalysis
• P-chirality
• monodentate phosphines
• transannulation
• 1,2,3-thiadiazole

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work is financially supported by the National Natural Science Foundation of China (no. 21602010), and the Fundamental Research Funds for the Central Universities (nos. XK1802-6 and 12060093063).