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

Molecular Diversity
Alireza VarmazyarSamira Arab-Salmanabadi

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.

References

Jul 10, 1992·Journal of Medicinal Chemistry·G C CrawleyJ M Giroaeau
May 31, 2002·Journal of Medicinal Chemistry·John C DanilewiczDavid J Rance
Sep 2, 2010·Bioorganic & Medicinal Chemistry Letters·Craig JamiesonLynn Smith
Nov 13, 2013·Organic Letters·Guohua LiangNancy I Totah
Apr 17, 2014·Journal of the American Chemical Society·Daishi FujinoAtsuhiro Osuka
Jun 19, 2018·The Journal of Organic Chemistry·Andrei G KutateladzeTina Holt

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Methods Mentioned

BETA
column chromatography

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