Organocatalytic site- and stereoselective 1, 6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides. Issue 21 (1st October 2020)

• Record Type: Journal Article
• Authors: Li, Fushuai; Chen, Xuling; Liang, Shuai; Shi, Zhenyan; Li, Pengfei; Li, Wenjun
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 21(2020)
• Page Start: 3446
• Page End: 3451
• Publication Date: 2020-10-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo00888e
• Languages: English
• ISSNs: 2052-4110

Abstract

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 for the first time. 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.