6273-94-5Relevant articles and documents
A novel C-C bond formation by Baylis-Hillman type reaction mediated by SmI2: An effective approach to α-hydroxyalkylacrylamide synthesis
Youn,Park,Kim
, p. 2005 - 2006 (2000)
α-Bromoacrylamides (1) reacted with aldehydes or ketones, in the presence of SmI2 at - 78 °C in THF, within 5 min to produce Baylis-Hillman type reaction products (2) through an anionic process using vinylsamarium Grignard species in good yield
Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights
Kurouchi, Hiroaki,Sai, Masahiro
supporting information, p. 3585 - 3591 (2021/06/27)
We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).
Rh(i)-Catalyzed regioselective arylcarboxylation of acrylamides with arylboronic acids and CO2
Cai, Lei,Fu, Lei,Gao, Yuzhen,Li, Gang,Li, Shangda,Zhou, Chunlin
supporting information, p. 7328 - 7332 (2020/11/19)
The first Rh(i)-catalyzed regioselective arylcarboxylation of electron-deficient acrylamides with arylboronic acids under atmospheric pressure of CO2 has been developed. A range of acrylamides and arylboronic acids were compatible with this reaction under redox-neutral conditions, leading to a series of malonate derivatives that are versatile building blocks in organic syntheses.
