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Synfacts 2014; 10(1): 0068
DOI: 10.1055/s-0033-1340458
DOI: 10.1055/s-0033-1340458
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Oxazinoindoles via Gold-Catalyzed Stereoselective Cascade Reaction
Further Information
Publication History
Publication Date:
13 December 2013 (online)

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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