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Y(OTf)3 catalyzed substitution dependent oxidative C(sp)–C(sp) cleavage and regioselective dehydration of β-allyl-β-hydroxydithioesters: alternate route to α,β-unsaturated ketones and functionalized dienes |
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| Authors: | Sushobhan Chowdhury Tanmoy Chanda Ganesh Chandra Nandi Suvajit Koley B. Janaki Ramulu S.K. Pandey Maya Shankar Singh |
| Affiliation: | 1. Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi 221005, India;2. Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USA;3. School of Chemistry and Biochemistry, Thapar University, Patiala 147004, India |
| 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. |
| Keywords: | Regioselective allylation Yttrium(III)triflate C&ndash C activation and cleavage Allylic isomerization α,β-Unsaturated ketone Selective dehydration Functionalized diene |
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