Efficient Synthesis of N-Carbamoylpropargylamines from α-Amido Sulfones Using Dimethylalkynylaluminum Reagents

Abstract

Dimethylalkynylaluminum reagents derived from terminal alkynes and trimethylaluminum underwent addition to various N-activated α-amido sulfones to produce the corresponding alkynylamines in moderate to excellent yields. The optimized protocol avoids the preparation and isolation of relatively unstable N-activated imines that are generated in situ from their corresponding, stable, N-activated α-amido sulfones. This methodology provides access to a wide range of alkynylamines containing N-carbamoyl, -acyl, and -sulfonyl moieties.

Key words

dimethylalkynylaluminum reagents - nucleophilic addition - propargylamines - N-activated α-amido sulfones - alkynylamines

Publication History

Received: 24 November 2021

Accepted: 24 November 2021

Article published online:
20 January 2022

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