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Synfacts 2014; 10(1): 0068
DOI: 10.1055/s-0033-1340458
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Oxazinoindoles via Gold-Catalyzed Stereoselective Cascade Reaction

Contributor(s):
Hisashi Yamamoto
,
Mahiuddin Baidya
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
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Publication History

Publication Date:
13 December 2013 (online)

 
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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.


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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).


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