Chiarucci M, Mocci R, Syntrivanis L.-D, Cera G, Mazzanti A, Bandini M * University
of Bologna, Italy
Merging Synthesis and Enantioselective Functionalization of Indoles by a Gold-Catalyzed
Asymmetric Cascade Reaction.
Angew. Chem. Int. Ed. 2013;
52: 10850-10853
Key words
gold - oxazinoindoles - hydroamination
Significance
The authors developed a gold-catalyzed hydroamination followed by an asymmetric nucleophilic
allylic substitution cascade to access oxazino[4,3-a]indoles in good yields and enantioselectivities. Owing to pharmacologically active
indole alkaloids, this rapid synthesis and asymmetric decoration of the polycyclic
indolyl core is highly important.
Comment
Amazingly, the stereodifferentiating event in this gold-catalyzed asymmetric domino
process takes place at the late stage, which is somewhat unusual and more challenging.
Extensive mechanistic studies support the stepwise SN2′-type mechanism for the final allylic alkylation ring closure (cycle II).
