Jump to main content
Jump to site search

Issue 21, 2020
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


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

Org. Chem. Front., 2020,7, 3446-3451
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, 7, 3446
DOI: 10.1039/D0QO00888E

Social activity

Search articles by author

Spotlight

Advertisements