Titanium Tetrachloride‐Mediated Approach to Access 2‐Chloro‐2‐Substituted Isoindolin‐1‐ones through the Addition of Alkynes to Acyliminium ions

An asymmetric approach to access 2‐substituted isoindolin‐1‐ones 9–11 was developed through TiCl4‐mediated addition‐chlorination of N,O‐acetals 7 a–7 c with terminal alkynes 8. A range of substrates were amenable to this transformation, and the desired substituted isoindolin‐1‐ones were obtained in...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-05, Vol.2021 (18), p.2625-2633
Main Authors: Xu, Wen‐Ke, Guo, Jia‐Ming, Chen, Zhao‐Dan, Si, Chang‐Mei, Wei, Bang‐Guo
Format: Article
Language:English
Subjects:
Acetals
Alkynes
Chiral isoindolinone scaffolds
Diastereoselectivity
Lewis acids
N,O-acetal
Substitutes
Substrates
Terminal alkynes
Titanium chlorides
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Summary:An asymmetric approach to access 2‐substituted isoindolin‐1‐ones 9–11 was developed through TiCl4‐mediated addition‐chlorination of N,O‐acetals 7 a–7 c with terminal alkynes 8. A range of substrates were amenable to this transformation, and the desired substituted isoindolin‐1‐ones were obtained in moderate to good yields with moderate diastereoselectivities. An efficient method to obtain 2‐substituted isoindolin‐1‐ones have been established by TiCl4‐mediated addition‐chlorination of N,O‐acetals with terminal alkynes. A range of substrates were amenable to this transformation, and a series of desired substituted isoindolin‐1‐ones were obtained in moderate to good yields with moderate diastereoselectivities. Moreover, the one pot chlorination is an additional advantage of this method.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100368