Origins of Diastereoselectivity of 1,3-Dipolar Cycloadditions of Cyclic Azomethine Ylides and Nitrones to Cyclopentenes

Shuangshuang Cai; Shaohong Wang; Silong Xu; Xin-Hua Duan; X D Liu; K N Houk; Pengchen Ma

doi:10.1021/acs.joc.6c00133

May 10, 2026The Journal of Organic Chemistry

Origins of Diastereoselectivity of 1,3-Dipolar Cycloadditions of Cyclic Azomethine Ylides and Nitrones to Cyclopentenes

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Key Points

This research aims to understand the factors influencing diastereoselectivity in cycloadditions involving cyclic azomethine ylides and nitrones.
Analyzed the reactivity of cyclic azomethine ylides and nitrones in 1,3-dipolar cycloadditions
Studied electronic and steric effects affecting selectivity
Assessed different pathways leading to varying diastereoselectivity
Identified distinct electronic effects as a key factor in selectivity trends
Demonstrated that steric factors also play a significant role
Provided a comprehensive understanding of reactivity patterns in 1,3-dipolar cycloadditions

Implication

Experimental analysis demonstrates how azomethine ylides and nitrones affect selectivity in cyclopentene reactions, implying deeper chemical insights.

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Cite This Study

Cai et al. (2026) studied this question.

synapsesocial.com/papers/6a04147679e20c90b4444632 https://doi.org/10.1021/acs.joc.6c00133

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Origins of Diastereoselectivity of 1,3-Dipolar Cycloadditions of Cyclic Azomethine Ylides and Nitrones to Cyclopentenes

Key Points

Implication

Discussion

Cite This Study

Origins of Diastereoselectivity of 1,3-Dipolar Cycloadditions of Cyclic Azomethine Ylides and Nitrones to Cyclopentenes

Key Points

Implication

Discussion

Cite This Study

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