Phosphine-Catalyzed Regio- and Stereoselective Umpolung Addition of Amides to Alkynoates: Access to Complex α,β-Dehydroamino Acid Derivatives

Organic Letters 2026 Open access

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Authors: Nicklas W. Buchbinder, Kyle Dunnavant, Andrew D. Bage, Owen N. Beck, Kaamia R. Harris, Reilly K. Gwinn, Webster L. Santos
DOI: 10.1021/acs.orglett.5c04858
Cited by: 0
References: 39

Abstract

Abstract Accessing complex α,β-dehydroamino acids remains challenging due to the instability of the enamine product during N-terminal deprotection. We report a mild, organocatalytic method for the installation of primary amides on the α-carbon of alkynoates that avoids N-terminal deprotection. The PBu3 catalyst is key to umpolung reactivity and affords α,β-dehydroamino acids in good yield with excellent (Z)-selectivity. The utility of this reaction was demonstrated in the synthesis of two natural products: a 2,5-diketopiperazine and scutianene M.

Fields of Study & Subjects

Asymmetric Synthesis and Catalysis Advanced Synthetic Organic Chemistry Catalytic Alkyne Reactions

Publication details

Journal / source
Organic Letters
Volume
28
Issue
20
Pages
6159–6164
Publication date
29 January 2026
Language
EN