DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes.

Org Lett

School of Chemistry and Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi'an 710049, P. R. China.

Published: December 2024

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates with electron-poor alkenes , which affords exocyclic olefinic cyclohexenes in good yields and excellent regio-, diastereo-, and / selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates use the β- and ε-carbons for the bond formation, presenting new and regiodivergent C synthons for Lewis base-catalyzed annulations.

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http://dx.doi.org/10.1021/acs.orglett.4c03842DOI Listing

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