Premium
Trifluorosulfonylation Cascade in Allenols: Stereocontrolled Synthesis of Bis(triflyl)enones
Author(s) -
LázaroMilla Carlos,
Macicior Jon,
Yanai Hikaru,
Almendros Pedro
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001236
Subject(s) - regioselectivity , selectivity , allylic rearrangement , electrophile , chemistry , cascade , catalysis , combinatorial chemistry , functional group , cascade reaction , molecule , organic chemistry , chromatography , polymer
Herein, we report investigations embodying the first example of reversal of the native regioselectivity in the reaction of allenols with electrophiles. The effortlessness of C−C bond formation, mild reaction conditions, neither catalysts nor light irradiation, and exquisite selectivity, both in terms of functional‐group tolerance and chemo‐, site‐, and stereo‐selectivity, converts this trifluorosulfonylation‐rearrangement sequence into an appealing protocol for the preparation of novel functionalized enones. The synthetic utility of this method has been validated by the conversion of the initially prepared bis(triflyl)enones into a variety of bis(triflyl)‐functionalized molecules such as 1,3‐dienes, allylic alcohols, pyrroles, pyrazoles, and chromenes. Besides, DFT calculations have provided a reliable understanding of observed selectivity.