Publication: Intramolecular Conjugate Ene Reaction of γ-Difluoromethyl- and γ-Trifluoromethyl-α,β-Unsaturated γ-Butyrolactones
Issued Date
2015-11-06
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ISSN
15206904
00223263
00223263
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2-s2.0-84946763259
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.80, No.21 (2015), 10512-10520
Suggested Citation
Watchara Srimontree, Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Intramolecular Conjugate Ene Reaction of γ-Difluoromethyl- and γ-Trifluoromethyl-α,β-Unsaturated γ-Butyrolactones. Journal of Organic Chemistry. Vol.80, No.21 (2015), 10512-10520. doi:10.1021/acs.joc.5b01562 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/35730
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Title
Intramolecular Conjugate Ene Reaction of γ-Difluoromethyl- and γ-Trifluoromethyl-α,β-Unsaturated γ-Butyrolactones
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Abstract
© 2015 American Chemical Society. A general synthetic strategy to cis-fused bicyclic γ-butyrolactones via the retro-Diels-Alder reaction/intramolecular conjugate ene cascade (RDA/ICE) reaction under the flash-vacuum pyrolysis of maleic anhydride adducts is developed. The reaction gave high yields of products with high stereoselectivity. The existence of the difluoromethyl or trifluoromethyl group at the γ-position of the in situ-generated homoalkenyl- or homoalkynyl-α,β-unsaturated γ-butyrolactones was found to accelerate the rate of the intramolecular conjugate ene reaction leading to γ-difluoromethylated and γ-trifluoromethylated cis-fused bicyclic γ-butyrolactones.