Synthesis of Fluorine‐Containing 3,3‐Disubstituted Oxetanes and Alkylidene Oxetanes

Abstract

Access to fluoroalkylidene-oxetanes and -azetidines was realized from 3-oxetanone, 3-azetidinone, and fluorosulfones through the Julia-Kocienski reaction. This approach allows the preparation of new precursors of fluorinated four-mem-

Photoinduced Nonstabilized Azomethine Ylide Formation for the Preparation of Fluorine Containing Pyrrolidines

“…19 F NMR (471 MHz, CDCl 3 ): δ −133.9 (quint, 4 J HF = 3.8 Hz). NMR data are in good agreement with literature data …”

“…The reaction occurred in the presence of EY (4 mol %) and 1 under irradiation with a house green LED (5 W) over 18 h at 20 °C. In this case, the corresponding pyrrolidine 4 was obtained in 56% yield, although the reaction reached up to 70−85% completion (determined by 19 F NMR analysis of the crude).…”

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

“…The preparation of a series of fluoroalkylidene-oxetanes 1-3 was previously reported from 3-oxetanone through an olefination reaction with benzothiazoyl sulfones (Scheme 1) [22]. With these fluoroalkylidene-oxetanes in hands, we studied the selectivity of ring-opening reactions with heteroatom nucleophiles in order to access tetrasubstituted fluoroalkenes.…”

Synthesis of Monofluoroalkenes: A Leap Forward

“…Since 2011, the Lequeux group has studied the synthesis of fluoroallylamines. [65][66][67][68][69] To access this class of compound, a Julia-Kocienski olefination was used as the key step. In most cases, good yields were obtained, but a lack of stereoselectivity was observed (Scheme 49).…”

“…In 2013, the Lequeux group also reported the preparation of a series of fluoroalkylidene-substituted cyclobutanes, oxetanes, and azetidines starting from the corresponding ketones (Scheme 207). 68 However, when a phosphono sulfone was reacted with the same starting ketones, a Horner-Wadsworth-Emmons olefination took place instead.…”