Au(I)/(R)‑BINOL–Ti(IV) Concerted Catalyzed Asymmetric Cascade Cycloaddition Reaction of Arylalkynols

Au(I)/(R)‑BINOL–Ti(IV) Concerted Catalyzed Asymmetric Cascade Cycloaddition Reaction of Arylalkynols

An efficient catalytic asymmetric cascade cycloaddition reaction of arylalkynols with dioxopyrrolidines was developed. This reaction was achieved using Au­(I) and (R)-BINOL–Ti­(IV) bimetallic catalysts and exclusively delivered a series of chiral oxo-bridged bicyclic benzooxacine compounds in up to...

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Veröffentlicht in:Organic letters 2021-05, Vol.23 (9), p.3573-3577
Hauptverfasser: Wang, Hongkai, Zeng, Tianlong, Chang, Weixing, Liu, Lingyan, Li, Jing
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient catalytic asymmetric cascade cycloaddition reaction of arylalkynols with dioxopyrrolidines was developed. This reaction was achieved using Au­(I) and (R)-BINOL–Ti­(IV) bimetallic catalysts and exclusively delivered a series of chiral oxo-bridged bicyclic benzooxacine compounds in up to 86% yield with 96% ee as well as >33:1 dr. Meanwhile, three new σ bonds and three new stereogenic centers were formed in a one-pot process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00976