Efficient synthesis of tetracyclic γ-lactams via gold-catalyzed oxidative cyclization of alkenyl diynes

An efficient gold-catalyzed cascade cyclization of alkenyl diynes involving alkyne oxidation, carbene-alkyne metathesis and cyclopropanation has been developed, furnishing a series of tetracyclic γ-lactams bearing one quaternary carbon center and one tertiary carbon center in moderate to good yields...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (9), p.2557-2562
Main Authors: Chong-Yang, Shi, Ji-Jia, Zhou, Pan, Hong, Bo-Han, Zhu, Feng-Lin, Hong, Peng-Cheng, Qian, Sun, Qing, Lu, Xin, Long-Wu, Ye
Format: Article
Language:English
Subjects:
Alkynes
Carbon
Chemical synthesis
Gold
Metathesis
Organic chemistry
Oxidation
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Summary:An efficient gold-catalyzed cascade cyclization of alkenyl diynes involving alkyne oxidation, carbene-alkyne metathesis and cyclopropanation has been developed, furnishing a series of tetracyclic γ-lactams bearing one quaternary carbon center and one tertiary carbon center in moderate to good yields with excellent diastereoselectivities. In addition, the proposed mechanistic rationale for this oxidative cyclization is well supported by theoretical calculations.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00123c