861303-48-2Relevant academic research and scientific papers
On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access β2-Amino Ketones
Chang, Sukbok,Heo, Joon,Kim, Dongwook,Lee, Minhan
supporting information, p. 3667 - 3675 (2022/03/02)
β2-Amino carbonyls, an α-substituted β-amino scaffold, hold a prominent place in the development of new pharmaceuticals and peptidomimetics. Herein, we report a highly efficient Rh-catalyzed ring-opening amidation of substituted cyclopropanols, which turned out to serve as a linchpin for the selective synthesis of β2-amino ketones to outcompete the formation of β3-isomers. Instead of the generally accepted rationale to consider steric factors for the β2-selectivity, orbital interaction was elucidated to play a more critical role in the amidative ring-opening of cyclopropanols to generate the key Rh-C intermediate. Subsequent inner-sphere acylnitrene transfer was achieved in excellent efficiency (TON > 5000) by using readily accessible dioxazolones as the amino source to afford β2-amino ketones with broad applicability.
Efficient Br?nsted acid-catalyzed aza-Michael reaction of amides and ureas with α,β-unsaturated enones under high-pressure conditions
Azad, Saleha,Kobayashi, Tomohiro,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
scheme or table, p. 48 - 50 (2009/04/11)
A new strategy for the aza-Michael reaction of amides and ureas with α,β-unsaturated enones, which uses p-TsOH·H2O as an efficient and inexpensive catalyst under high-pressure conditions, has been developed.
