Regioselective dehydrative intramolecular heteroannulation of β-allyl-β-hydroxy dithioesters: facile and straightforward entry to 2H-thiopyrans

Chowdhury, Sushobhan ; Chanda, Tanmoy ; Koley, Suvajit ; Ramulu, B. Janaki ; Raghuvanshi, Keshav ; Singh, Maya Shankar (2014) Regioselective dehydrative intramolecular heteroannulation of β-allyl-β-hydroxy dithioesters: facile and straightforward entry to 2H-thiopyrans Tetrahedron, 70 (4). pp. 914-918. ISSN 0040-4020

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Official URL: http://doi.org/10.1016/j.tet.2013.12.020

Related URL: http://dx.doi.org/10.1016/j.tet.2013.12.020

Abstract

β-Allyl-β-hydroxy dithioesters have been employed in the synthesis of hitherto unreported and synthetically demanding 2H-thiopyrans via regioselective intramolecular annulation strategy. Lewis acid BF3·Et2O efficiently mediates the regioselective dehydration followed by intramolecular thioannulation at room temperature. The attractive features of this protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product.

Item Type:Article
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Deposited On:15 Jun 2021 11:35
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