Issue 13, 2021

Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines

Abstract

We developed a synthetic method for α-(aminoethyl)-α,β-enones from aryl-substituted homopropargyl sulfonamides and aldehydes, representing the first synthesis of conjugated enones via alkyne aza-Prins cyclization. These products could be converted into pyrrolidines by a formal 5-endo-trig cyclization.

Graphical abstract: Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines

Supplementary files

Article information

Article type
Paper
Submitted
14 Jan 2021
Accepted
11 Mar 2021
First published
11 Mar 2021

Org. Biomol. Chem., 2021,19, 2959-2967

Author version available

Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines

S. Amemiya, S. Okemoto, A. Tsubouchi and A. Saito, Org. Biomol. Chem., 2021, 19, 2959 DOI: 10.1039/D1OB00072A

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