Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates

Roohollah Kazem Shiroodi, Vladimir Gevorgyan

Research output: Contribution to journalArticle

156 Scopus citations

Abstract

Propargylic esters and phosphates are easily accessible substrates, which exhibit rich and tunable reactivities in the presence of transition metal catalysts. π-Acidic metals, mostly gold and platinum salts, activate these substrates for an initial 1,2- or 1,3-acyloxy and phosphatyloxy migration process to form reactive intermediates. These intermediates are able to undergo further cascade reactions leading to a variety of diverse structures. This tutorial review systematically introduces the double migratory reactions of propargylic esters and phosphates as a novel synthetic method, in which further cascade reaction of the reactive intermediate is accompanied by a second migration of a different group, thus offering a rapid route to a wide range of functionalized products. The serendipitous observations, as well as designed approaches involving the double migratory cascade reactions, will be discussed with emphasis placed on the mechanistic aspects and the synthetic utilities of the obtained products.

Original languageEnglish (US)
Pages (from-to)4991-5001
Number of pages11
JournalChemical Society Reviews
Volume42
Issue number12
DOIs
StatePublished - May 28 2013

ASJC Scopus subject areas

  • Chemistry(all)

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