4.5 Article

Domino ring opening/cyclization of oxiranes for synthesis of functionalized 2H-pyran-5-carboxylate

Journal

MOLECULAR DIVERSITY
Volume 24, Issue 3, Pages 707-716

Publisher

SPRINGER
DOI: 10.1007/s11030-019-09978-9

Keywords

2H-pyrans; Oxirane; Copper acetylide; Hexafluoroisopropyl alcohol; Malonate

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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-digcyclization 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. [GRAPHICS] .

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