Abstract
AbstractThe chiral pool material (–)‐levoglucosenone (6,8‐dioxabicyclo[3.2.1]oct‐2‐en‐4‐one, LGO) has been substituted by using a series of Pd‐mediated cross‐coupling reactions. Iodination of LGO followed by Suzuki–Miyaura cross‐coupling reaction with boronic acids by employing the Buchwald ligand SPhos with Pd(OAc)2 afforded 3‐aryl derivatives in excellent yields. Selective Heck arylation reaction at the 2‐position was achieved with aryl iodides with K3PO4 as base and SPhos ligand with Pd(OAc)2 (1–5 mol‐%). A selective hydroarylation reaction (formal conjugate addition) was developed by using the same aryl iodides, benzyldiethylamine, Pd(OAc)2, and P(o‐tol)3. The products were converted, either directly or after alkene reduction, through a Baeyer–Villiger oxidation into chiral 3‐ and 4‐substituted 5‐(hydroxymethyl)dihydrofuran‐2(3H)‐ones.
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