Stereospecific alkyl-alkyl cross-coupling of boronic esters - Nature

"More recently, enantiomerically enriched boronic esters have shown great promise in modular synthesis as versatile building blocks for the rapid construction of diverse molecules. A significant challenge in this area is to employ boronic esters for the catalytic construction of C(sp 3)-C(sp 3) bonds, especially those where the reaction site is a stereogenic carbon center. Addressing this challenge would not only expand the utility of boronic esters in the modular synthesis"

"1 In this connection, we have developed a stereospecific C(sp 3)-C(sp 3) coupling reaction catalyzed by a copper acetylide complex. This reaction operates with four-coordinate boron "ate" complexes while remaining inert to simple functional groups including boronic esters, and thereby enables efficient strategies for modular synthesis of complex molecules. Applications to the synthesis of (-)-spongidepsin and the carbon skeleton of fluvirucinine A 1 are described."

A stereospecific C(sp3)-C(sp3) coupling reaction is catalyzed by a copper acetylide complex and engages four-coordinate boron "ate" complexes. The reaction remains inert to simple functional groups, including boronic esters, enabling selective cross-coupling at stereogenic carbon centers. Enantiomerically enriched boronic esters serve as versatile building blocks for rapid construction of diverse molecular frameworks via this modular approach. The method addresses challenges in catalytic construction of C(sp3)-C(sp3) bonds at stereogenic sites and expands the utility of boronic esters in synthesizing natural products and bioactive molecules. Applications include synthesis of (-)-spongidepsin and the carbon skeleton of fluvirucinine A1.

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