Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro-Stephens Coupling/Alkyne Reduction Tandem Reactions

Wei Li, Christopher M. Schneider, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A copper-mediated macrocyclization involving the reaction of a vinyl iodide and a terminal alkyne followed by an in situ reduction of the enyne intermediate is reported. The reaction generates a conjugated Z-double bond within a strained medium-size lactone, lactam, or ether macrocycle. A variety of macrocyclic compounds bearing different ring sizes and functionalities were synthesized. A complementary stepwise procedure was also developed for less strained ring systems.

Original languageEnglish (US)
Pages (from-to)3902-3905
Number of pages4
JournalOrganic Letters
Volume17
Issue number15
DOIs
StatePublished - Aug 7 2015

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