期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 41, 页码 8983-8989出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001236
关键词
allenes; fluorine; metal-free reactions; selectivity; synthetic methods
资金
- AEI (MICIU) [PGC2018-095025-B-I00]
- FEDER [PGC2018-095025-B-I00]
- KAKENHI [17K08224]
- Grants-in-Aid for Scientific Research [17K08224] Funding Source: KAKEN
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.
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