Synfacts 2021; 17(12): 1345
DOI: 10.1055/s-0041-1737074
Metals in Synthesis

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

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
Xie Q, Dong G. * University of Chicago, USA
Aza-Matteson Reactions via Controlled Mono- and Double-Methylene Insertions into Nitrogen–Boron Bonds.

J. Am. Chem. Soc. 2021;
143: 14422-14427
DOI: 10.1021/jacs.1c06186.
 

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.


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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.


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Publication History

Publication Date:
17 November 2021 (online)

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