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Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides

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Abstract

A chiral phosphoric acid catalyzed site-selective 1,6-conjugate addition of N-aryl-3-oxobutanamides to in situ formed propargylic aza-p-quinone methides from propargylic alcohols has been established and this represents the first report on organocatalytic site- and stereoselective 1,6-conjugate addition of propargylic aza-para-quinone methides. Furthermore, the synthetic strategy enables the formation of diarylmethyl alkynes bearing vicinal quaternary and tertiary carbon stereocenters in high yields with high asymmetric induction.

Graphical abstract: Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides

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Article information


Submitted
28 Jul 2020
Accepted
21 Sep 2020
First published
24 Sep 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides

F. Li, X. Chen, S. Liang, Z. Shi, P. Li and W. Li, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00888E

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