Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides
We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.
Iodine-mediated oxidative dehydrogenation of β-acylamino ketones for the highly stereoselective synthesis of (Z)-β-keto-enamides
An iodine-mediated oxidative dehydrogenation of β-acylamino ketones has been developed for the synthesis of β-ketoenamides in moderate to good yields. Only Z-isomers are accessed due to the intramolecular H-bonding interaction in the HI-elimination step.
Chang, Hong-Hong,Hu, Fei,Gao, Wen-Chao,Liu, Tao,Li, Xing,Wei, Wen-Long,Qiao, Yan
supporting information
p. 1592 - 1596
(2016/06/14)
Preparation of highly substituted (β-acylamino)acrylates via iron-catalyzed alkoxycarbonylation of N-vinylacetamides with carbazates
An efficient iron(ii)-catalyzed alkoxycarbonylation reaction between N-vinylacetamides and carbazates is reported. The corresponding useful highly substituted (β-acylamino)acrylates could be obtained in reasonable to good yields and stereoselectivity under mild reaction conditions. This journal is