Ca(NTf2)2/HFIP‐Mediated Direct and Mild Rearrangement of Cyclopropyl Carbinols to E‐Homoallylic Triflimides. Issue 36 (22nd September 2022)

• Record Type: Journal Article
• Authors: Wu, Min; Duan, Zhiqiang; Liu, Qingmei; Gao, Hui; Zhou, Zhi; Yi, Wei; Wang, Shengdong
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 36(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-22
• Subjects: Calcium -- Cyclopropyl carbinols -- Hexafluoroisopropanol -- Homoallylic triflimides -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200813
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Unsaturated triflimides, especially homoallylic triflimide species, are rarely assessable. Herein, we disclose a Ca(NTf2 )2 /HFIP‐mediated direct chemo‐, regio‐, and stereoselective rearrangement of diverse cyclopropyl carbinols to exclusive E ‐homoallylic triflimides in moderate to excellent yields at room temperature, in which Ca(NTf2 )2 was used as both the OH activator and the triflimide anion source. This protocol shows excellent substrate/functional group tolerance with an emphasis on those substrates bearing strong electron‐withdrawing functional groups. Abstract : A novel, general and straightforward Ca(NTf2 )2 /HFIP‐mediated rearrangement of cyclopropyl carbinols for the construction of E ‐homoallylic triflimides has been developed. In this protocol, Ca(NTf2 )2 was used as both the OH activator and the triflimide anion source. This transformation takes place under mild conditions and shows an impressive substrate and functional group tolerance.