Activation of Marginally Reactive Boron Enolates by MeLi for the Formation of Enol Phosphates and Synthesis of the Δ(9)-THC Intermediate

The Journal of Organic Chemistry
Hiroki KawadaYuichi Kobayashi

Abstract

The addition of MeLi to boron enolates produced by the 1,4-addition of Ar2Cu(CN)Li2 to BF3·OEt2-activated enones was followed by the reaction with ClP(O)(OEt)2 to afford the corresponding enol phosphates in moderate to good yields. The scope of this method was examined with sterically hindered or electronically biased enones and/or reagents. This activation of boron enolates was successfully applied to the synthesis of the methyl ether of Δ(9)-tetrahydrocannabinol.

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Citations

Apr 8, 2020·Organic & Biomolecular Chemistry·Victor R L J BloemendalFloris P J T Rutjes
Aug 12, 2020·Chemistry : a European Journal·Anderson R AguillónRodrigo O M A de Souza

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