A carbene-catalyzed enantio-and diastereoselective [2 + 4] cycloaddition reaction is developed for quick and efficient access to structurally complex multicyclic pyrano[2,3-c]pyrazole molecules. The reaction tolerates a broad scope of substrates bearing various substitution patterns, with the multicyclic pyrano-[2,3-c]pyrazole products afforded in generally good to excellent yields and optical purities. The chiral molecules obtained from this approach has found promising applications in the development of novel bacteriacides for plant protection.
An N-heterocyclic carbene (NHC)-catalyzed atroposelective annulation reaction is disclosed for quick and efficient access to thiazine derivatives. A series of axially chiral thiazine derivatives bearing various substituents and substitution patterns were produced in moderate to high yields with moderate to excellent optical purities. Preliminary studies revealed that some of our products exhibit promising antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) that causes rice bacterial blight.
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