3 years ago

Rapid Access to Nitrogenous Heterobicycles via RhIII-Catalyzed Isomerization from Alkynes to Allenes

Rapid Access to Nitrogenous Heterobicycles via RhIII-Catalyzed Isomerization from Alkynes to Allenes
Yoshinori Sato, Masahiro Terada, Keisuke Takeda, Itaru Nakamura
We show that N-alkynylnitrones are efficiently converted to nitrogenous heterobicyclic compounds with a nitrogen atom at the bridgehead position by using a RhIII-catalyst. Our mechanistic studies suggest that the reaction proceeds via an allene intermediate, which is generated in situ through RhIII-catalyzed isomerization of the alkyne group. Closing rings: A RhIII catalyst rapidly constructs heterobicycles from N-alkynylnitrones. Mechanistic studies suggest that the present transformation proceeds via in situ generation of an allene intermediate through Rh-catalyzed isomerization of an alkyne.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701704

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