Synthesis of fluorinated building blocks based on spiro[3.3]heptane scaffold. Issue 7 (18th February 2016)

• Record Type: Journal Article
• Authors: Chernykh, Anton V.; Feskov, Illia O.; Chernykh, Alla V.; Daniliuc, Constantin G.; Tolmachova, Nataliya A.; Volochnyuk, Dmitriy M.; Radchenko, Dmytro S.
• Is Part Of: Tetrahedron. Volume 72:Issue 7(2016)
• Page Start: 1036
• Page End: 1041
• Publication Date: 2016-02-18
• Subjects: Fluorine -- Conformational restriction -- Non-flattened building blocks -- Spiro compounds; LGPCTMRNPRKHPR-UHFFFAOYSA-N -- KNHIUDDGPFPSFP-UHFFFAOYSA-N -- OVKHXHWMYZNQNR-IZLXSQMJSA-N -- OVKHXHWMYZNQNR-OLQVQODUSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.12.081
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: New non-flattened amino group-containing building blocks and fluorinated analogs based on the spiro[3.3]heptane motif were synthesized. The syntheses included a challenging deoxofluorination of sterically hindered carbonyl groups via an intermediate carbocation. The synthesized compounds could be useful in medicinal chemistry due to their three-dimensional shape, and a different pattern of the fluorine substitution. Graphical abstract: