Enantioselective Alkylation of Amino Acid Derivatives with ­Unactivated Olefins via C–N Bond Cleavage

Yue-Ming Cai; Ming Shang

doi:10.1055/s-0042-1752337

Synlett, Table of Contents

Synlett 2023; 34(08): 875-881
DOI: 10.1055/s-0042-1752337

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Enantioselective Alkylation of Amino Acid Derivatives with Unactivated Olefins via C–N Bond Cleavage

Yue-Ming Cai

,

Ming Shang∗

Abstract

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Abstract

We reported a nickel-catalyzed enantioconvergent deaminative alkylation of α-amino acid derivatives with unactivated olefins, providing an efficient and convenient access to a range of α-enantioenriched amides. This method represents the first example of enantioselective deaminative functionalization with racemic amine precursors and features in mild conditions and broad substrate scope. New sterically encumbered bis(oxazoline) ligand was developed to improve both reactivity and enantioselectivity, which is key to the success of this reaction.

Key words

deaminative alkylation - enantioselective - chiral bis(oxazoline) ligands - α-amino acid - sp³ cross-coupling

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References

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Enantioselective Alkylation of Amino Acid Derivatives with ­Unactivated Olefins via C–N Bond Cleavage

Enantioselective Alkylation of Amino Acid Derivatives with Unactivated Olefins via C–N Bond Cleavage