2024-03-28T22:32:27Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:00024545
2023-01-16T04:14:56Z
1903:1904:1905
Electrophilic Derivatization of Trifluoromethyl-Substituted Semisquarate Using Unsaturated Organosilanes and Subsequent Ring Transformations
Kurohara, Takashi
72635
Shibuya, Masatoshi
72636
Yamamoto, Yoshihiko
72637
To extend the synthetic potential of trifluoromethyl-substituted semisquarate (CF3-semisquarate) previously synthesized by us as a pluripotent building block, its electrophilic derivatization was investigated. The electrophilic addition of allylic silanes and silyl enolates to CF3-semisquarate afforded the corresponding 4-hydroxycyclobutenones. Subsequent ring expansion of these products via thermolysis or oxidation using lead tetraacetate afforded trifluoromethylated bicyclo[3.2.0]heptenones or (Z)-γ-alkylidenetetronates.
journal article
Wiley
2017-04-17
application/pdf
Advanced Synthesis & Catalysis
8
359
1413
1419
http://doi.org/10.1002/adsc.201601297
http://hdl.handle.net/2237/26757
1615-4150
https://nagoya.repo.nii.ac.jp/record/24545/files/ASC_update_MS_Rev.pdf
eng
https://doi.org/10.1002/adsc.201601297
This is the peer reviewed version of the following article: [T. Kurohara, M. Shibuya, Y. Yamamoto, Adv. Synth. Catal. 2017, 359, 1413.], which has been published in final form at [http://doi.org/10.1002/adsc.201601297]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.