Convenient synthesis of tricyclic N(1)-C(2)-fused oxazino-indolones via [Au(i)] catalyzed hydrocarboxylation of allenes

A new [Au(i)] catalyzed intramolecular hydrocarboxylation of allenes is presented as a valuable synthetic route to oxazino-indolones. The use of 3,5-(CF3)(2)-C6H3-ImPyAuSbF(6) as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts towards an enantioselective version (81 : 19 er) are also documented by means of a new family of chiral C-1-symmetric ImPyAuCl complexes.

Automated summary

A new Au(i) catalyzed intramolecular hydrocarboxylation of allenes is presented, which serves as a valuable synthetic route to oxazino-indolones. The use of 3,5-(CF3)(2)-C6H3-ImPyAuSbF(6) as the optimal catalyst allows for wide tolerance of functional groups, mild reaction conditions, and high yields. Preliminary attempts towards an enantioselective version are also documented using a new family of chiral C-1-symmetric ImPyAuCl complexes.