Matteson asymmetric homologation

Scheme1.2 Application of the Matteson asymmetric homologation to the synthesis of chiral a-aminoboronic esters.

Pietruska and coworkers reported asymmetric cyclopropanation of chiral B-vinyl-l,3,2-dioxaborolanes with diazomethane in the presence of Pd catalyst 58) (Figure 14). The cyclopropylboronates were utilized for subsequent reactions, such as Suzuki coupling, Matteson homologation, etc. 

The treatment of arylboronic acids and esters with alkaline hydrogen peroxide to produce the corresponding phenols was first reported more than 75 years ago [324]. The oxidation of alkyl- and alkenyl- boronic acid derivatives leads to alkanols [40] and alde-hydes/ketones, respectively [85, 257, 279, 316]. With a-chiral alkylboronates, the re-action proceeds by retention of configuration (Equation 53, Figure 1.32) [359, 121]. In fact, the oxidation of boronic acids and esters is a synthetically useful process, mainly in the preparation of chiral aliphatic alcohols via asymmetric hydroboration reactions [300, 302], or from Matteson homologation chemistry [322]. Paradoxically, the... 

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