Regio- and Stereoselective Addition of Brønsted Acids to Yndiamides: Synthesis of N,O,N- and N,S,N-Trisubstituted Ketene Acetals

Olivia L. Garry; Steven J. Mansfield; Edward A. Anderson

doi:10.1055/a-1638-5783

Synthesis, Table of Contents

Synthesis 2021; 53(22): 4221-4230
DOI: 10.1055/a-1638-5783

special topic

Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

Regio- and Stereoselective Addition of Brønsted Acids to Yndiamides: Synthesis of N,O,N- and N,S,N-Trisubstituted Ketene Acetals

Olivia L. Garry

,

Steven J. Mansfield

,

Edward A. Anderson∗

Abstract

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Abstract

Yndiamides, N,N-disubstituted alkynes, are versatile building blocks for the synthesis of nitrogen-containing organic molecules. Unlike ynamides, relatives that are inherently polarized by a single nitrogen substituent, their pseudo-symmetric nature renders regioselective reactions challenging. Here we report investigations into the regioselective addition of Brønsted acids to non-symmetric yndiamides, a reaction that delivers N,O,N- and N,S,N-trisubstituted ketene acetals with excellent regio- and stereoselectivity.

Key words

yndiamides - keteniminium ions - hydroalkoxylation - regioselectivity

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References

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