Aza-Matteson Homologations: Selective Mono- and Double-Carbenoid Insertions into Aminoboranes

Key words

aminoboranes - Matteson homologation - methylene insertion - tertiary amines

Significance

In 1963, Donald S. Matteson developed a valuable strategy allowing for carbenoid insertions into C–B bonds. While this homologation reaction has been thoroughly investigated, its extension to N–B bonds remained unexplored. The authors describe an aza-Matteson homologation leading to the selective construction of various α- and β-substituted amines, which are versatile, synthetically useful building blocks for further transformation.

Comment

Starting from readily accessible aminoboranes, the aza-Matteson reaction provides access to various α- and β-substituted amines in good yields. By the choice of the Lewis acid and leaving group attached to the carbenoid, selective mono- or double-methylene insertion is achieved. The synthetic utility of the method was demonstrated by the derivatization of biologically active compounds.

Publikationsverlauf

Artikel online veröffentlicht:
17. November 2021