Accessing Dihydroazepines and Cyclopentanes from Enynyl Ketones

Li Li; Shiqing Huang; Yingjian Gong; Jingpeng Han; Jianwei Liu; Genhong Wang; Baosheng Li

doi:10.1021/acs.orglett.5c04290

Abstract

The stereocontrolled construction of polycyclic architectures from linear precursors remains a significant challenge, particularly for medium-sized rings, where strain and conformational flexibility hinder efficient cyclization. Herein, we report a tandem cyclization strategy converting linear precursors to polysubstituted dihydroazepines. The resulting compounds undergo acid-promoted ring contraction to cyclopentanes with five contiguous stereocenters. Overall, this strategy provides a streamlined route to architecturally sterically congested azepine- and cyclopentane-fused dihydrofuran products with a broad substrate scope and functional group tolerance.

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Year: 2025
Type: article
Citations: 0
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APA Style

                            
                                    Li Li, 
                                
                                    Shiqing Huang, 
                                
                                    Yingjian Gong
                                
                                et al.
                            
                            (2025). 
                            Accessing Dihydroazepines and Cyclopentanes from Enynyl Ketones. 
                            Organic Letters
                            
                            .
                            https://doi.org/10.1021/acs.orglett.5c04290

Identifiers

DOI: 10.1021/acs.orglett.5c04290