Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement

Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement

A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the invo...

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Bibliographic Details
Main Authors: Huang, Nianyu, Liao, Hongze, Yao, Hui, Xie, Tianpeng, Zhang, Shasha, Zou, Kun, Liu, Xue-Wei
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Catalysts
Chemical Reactions
Online Access:https://hdl.handle.net/10356/144929
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Institution: Nanyang Technological University
Language: English
Description
Summary:A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the involvement of allenic ester as the glycosyl acceptor. A wide range of substrate scope with good to excellent yields was achieved with complete diastereoselectivity.

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