Catalyst-Free Domino Cross-Olefinations and Intramolecular Cyclizations of Morita–Baylis–Hillman Carbonates with Sulfur Ylides

A novel strategy for the catalyst-free domino cross-olefination and intramolecular cyclization of Morita-Baylis-Hillman carbonates with sulfur ylides has been established, resulting in the synthesis of 1,2-dihydroquinolines with a broad scope, excellent chemoselectivity, and high efficiency. Mechanistic experiments revealed the process of 1,1-dipole cross-olefination and highlighted the assistance of the amino group in achieving successful transformations.

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Publication Details

Journal
Organic Letters
Published
2024-08-19
DOI
https://doi.org/10.1021/acs.orglett.4c02639
Citations
10
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
2.50

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article

Catalyst-Free Domino Cross-Olefinations and Intramolecular Cyclizations of Morita–Baylis–Hillman Carbonates with Sulfur Ylides

You Huang, Yiming Zhou, Wei Cai
10 citations
Organic Letters
Cyclopropane Reaction Mechanisms
2.50
article

Catalyst-Free Domino Cross-Olefinations and Intramolecular Cyclizations of Morita–Baylis–Hillman Carbonates with Sulfur Ylides

You Huang, Yiming Zhou, Wei Cai
article en
10 citations

Abstract

A novel strategy for the catalyst-free domino cross-olefination and intramolecular cyclization of Morita-Baylis-Hillman carbonates with sulfur ylides has been established, resulting in the synthesis of 1,2-dihydroquinolines with a broad scope, excellent chemoselectivity, and high efficiency. Mechanistic experiments revealed the process of 1,1-dipole cross-olefination and highlighted the assistance of the amino group in achieving successful transformations.

Organic LettersVol. 26(34)
Nankai University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 11%
Cyclopropane Reaction Mechanisms
2.50
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