1447173-59-2Relevant academic research and scientific papers
Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides
Alexander, Juliana R.,Cook, Matthew J.
supporting information, p. 5822 - 5825 (2017/11/10)
A new approach for the formation of ketenimines via a decarboxylative allylic rearrangement pathway that does not require strong stabilizing or protecting groups has been developed. The products can be readily hydrolyzed into their corresponding secondary amides or reacted with sulfur ylides to perform an additional [2,3]-Wittig process. Mechanistic studies suggest an outer-sphere process in which reductive alkylation is rate-limiting.
Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu 3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals
Clark, Andrew J.,Filik, Robert P.,Thomas, Gerard H.,Sherringham, John
, p. 4094 - 4097 (2013/07/26)
2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule.
