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Domino ring opening/cyclization of oxiranes for synthesis of functionalized 2H-pyran-5-carboxylate
Alireza Varmazyar1, Sajjad Sedaghat2, Ahmad Nozad Goli-Kand1,3
1Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran, Iran.
Abstract:
A simple method for the synthesis of functionalized 2H-pyrans via a catalytic reaction of an oxirane, an alkyne, and a malonate has been developed in which a 6-exo-dig cyclization pathway is observed. In this transformation, the attack of in situ generated copper acetylides on oxiranes formed homopropargylic alcohol intermediates which further transferred to 2H-pyrans with the help of malonates.
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