Direct Synthesis of α-Amino Acid Derivatives by Hydrative Amination of Alkynes

Minghao Feng; Roberto Tinelli; Ricardo Meyrelles; Leticia González; Boris Maryasin; Nuno Maulide

doi:10.1002/anie.202212399

Direct Synthesis of α-Amino Acid Derivatives by Hydrative Amination of Alkynes

Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202212399. doi: 10.1002/anie.202212399. Epub 2022 Nov 29.

Authors

Minghao Feng¹, Roberto Tinelli^{1

2}, Ricardo Meyrelles^{1

3

2}, Leticia González³, Boris Maryasin^{1

3}, Nuno Maulide¹

Affiliations

¹ Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria.
² Vienna Doctoral School in Chemistry, University of Vienna, Währinger Strasse 42, 1090, Vienna, Austria.
³ Institute of Theoretical Chemistry, University of Vienna, Währinger Strasse 17, 1090, Vienna, Austria.

Abstract

α-Amino acid derivatives are key components of the molecules of life. The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we report a practical method for the preparation of α-amino acid derivatives via direct hydrative amination of activated alkynes under mild conditions, relying on sulfinamides as the nitrogen source. Computational studies suggest that the reaction is enabled by a new type of sulfonium [2,3]-sigmatropic rearrangement.

Keywords: Amination; Amino Acids; Reaction Mechanisms; Rearrangements; Ynamides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes* / chemistry
Amination
Amino Acids*

Substances

Alkynes
Amino Acids