Publication:
Intramolecular Conjugate Ene Reaction of γ-Difluoromethyl- and γ-Trifluoromethyl-α,β-Unsaturated γ-Butyrolactones

Issued Date

2015-11-06

Resource Type

Article

ISSN

15206904
00223263

DOI

10.1021/acs.joc.5b01562

Other identifier(s)

2-s2.0-84946763259

Rights

Mahidol University

Rights Holder(s)

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/20.500.14594/35730

Research Projects

Organizational Units

Authors

Journal Issue

Thesis

Title

Intramolecular Conjugate Ene Reaction of γ-Difluoromethyl- and γ-Trifluoromethyl-α,β-Unsaturated γ-Butyrolactones

Author(s)

Watchara Srimontree
 Chonticha Masusai
 Darunee Soorukram
 Chutima Kuhakarn
 Vichai Reutrakul
 Manat Pohmakotr

Other Contributor(s)

Mahidol University
 Khon Kaen University

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.

Keyword(s)

Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/35730

Collections

Scopus 2011-2015