Cu-Catalyzed Divergent Transformations of Allenylethylene Carbonates with Diboron Reagents

Org Lett. 2024 Feb 2;26(4):960-965. doi: 10.1021/acs.orglett.3c04316. Epub 2024 Jan 19.

Abstract

Divergent transformations of allenylethylene carbonates with diboron reagents catalyzed by copper are disclosed. By using CuCl/IPr·HCl as the catalyst, the allenylethylene carbonates react with B2hex2 to afford 2,4-dien-1-ols as the product in the presence of Cs2CO3 as the base, iPrOH as the additive, and 1,4-dioxane as the solvent. And they react with B2pin2 to form boronic half acids in the presence of NaOtBu as the base, water as the additive, and THF as the solvent. The reactions afford corresponding products in good stereoselectivities and yields, and further derivatizations of boronic half acids and study of the mechanism are also demonstrated.