Three-component coupling reactions that forge two carbon carbon bond formations in a single pot are important in that they provide key steps in building complex, bioactive molecules from simple starting materials with great efficiency. The conjugate addition reaction of organometallic reagents to Michael acceptors such as thiochromones and the subsequent functionalization of metal enolates will allow the formation of two carbon carbon bonds in one-pot operation. The hypothesis is that the in-situ formed metal enolates can be stabilized by various metal salts such as copper or zinc and utilized to form new carbon carbon bonds in highly selective fashion. Three-component reactions initiated by conjugate addition reactions of S-containing Michael acceptors such as thiochromones and derivatives with organometallic reagents catalyzed by metal salts are investigated. Excellent yields of functionalized 1,4-adducts can be isolated (&gt; 90%). The use of commercially available or easily prepared organometallic reagents will expedite the synthesis of a large library of these S-heterocycles from common starting materials.

Harnessing the reactivity of enolates in heterocycle synthesis

ACS Spring Meeting 2021

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