Y(OTf)3 catalyzed substitution dependent oxidative C(sp3)–C(sp3) cleavage and regioselective dehydration of β-allyl-β-hydroxydithioesters: alternate route to α,β-unsaturated ketones and functionalized dienes

Chowdhury, Sushobhan ; Chanda, Tanmoy ; Nandi, Ganesh Chandra ; Koley, Suvajit ; Janaki Ramulu, B. ; Pandey, S.K. ; Singh, Maya Shankar (2013) Y(OTf)3 catalyzed substitution dependent oxidative C(sp3)–C(sp3) cleavage and regioselective dehydration of β-allyl-β-hydroxydithioesters: alternate route to α,β-unsaturated ketones and functionalized dienes Tetrahedron, 69 (42). pp. 8899-8903. ISSN 0040-4020

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Official URL: http://doi.org/10.1016/j.tet.2013.07.092

Related URL: http://dx.doi.org/10.1016/j.tet.2013.07.092

Abstract

β-Allyl-β-hydroxydithioesters have been generated by the regioselective Grignard addition to the β-oxodithioesters. They have been successfully employed in selective C(sp3)–C(sp3) bond cleavage to construct α,β-unsaturated ketone residues by the treatment of an emerging catalyst yttrium(III)triflate for the first time. On the other hand, hetaryl substituted β-allyl-β-hydroxydithioesters led to the useful diene precursors through selective dehydration under the similar conditions.

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