Expanding the Potential of Heteroaryl Vinyl Sulfones

Article abstract of DOI:10.1021/acs.joc.6b01956

The easily available vinyl sulfone 3 showed great potential for new applications in several fields such as organic synthesis and bioconjugate formation. This was demonstrated by performing a systematic assessment of its reactivity in Michael, radical, and cycloaddition reactions. Heteroaryl vinyl sulfone 3 presented excellent output in terms of reactivity and selectivity, proving superior to phenyl vinyl sulfone 1 and with clear advantages over bis-sulfone 2. This behavior might be due to the conformational and orbital control exerted by the tetrazole unit according to DFT calculations. Moreover, some alternative transformations to the Julia-Kocienski olefination on the obtained products are also described.

Full text of DOI:10.1021/acs.joc.6b01956

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Article
Expanding the Potential of Heteroaryl Vinyl Sulfones
Eduardo Rodrigo, Inés Alonso, José Luis García Ruano, and M. Belén Cid
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.6b01956 • Publication Date (Web): 21 Oct 2016
Downloaded from http://pubs.acs.org on October 21, 2016
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