Clarification of the Reactivity of 1,3,3,3-Tetrafluoropropene Oxides

Yuji Tamura; Rina Yada; Tomoko Kawasaki-Takasuka; Tomohiro Agou; Toshio Kubota; Takashi Yamazaki

doi:10.1021/acs.orglett.0c00463

Clarification of the Reactivity of 1,3,3,3-Tetrafluoropropene Oxides

Org Lett. 2020 Mar 6;22(5):2044-2048. doi: 10.1021/acs.orglett.0c00463. Epub 2020 Feb 21.

Authors

Yuji Tamura¹, Rina Yada¹, Tomoko Kawasaki-Takasuka¹, Tomohiro Agou², Toshio Kubota², Takashi Yamazaki¹

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan.
² Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan.

PMID: 32083887
DOI: 10.1021/acs.orglett.0c00463

Abstract

Our computation has successfully clarified the reluctant behavior of trans- and cis-1,3,3,3-tetrafluoropropene oxides 1c toward nucleophiles and led to the expectation that these epoxides would react under the Brønsted acid activation conditions. Actually, this was the case, and these epoxides smoothly opened with CF₃SO₃H, whose elimination after the protection of the resultant OH group afforded the enol benzoates as the enolate precursors, which nicely allowed us to construct the corresponding aldol products by reactions with various aldehydes.