138835-05-9Relevant academic research and scientific papers
C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles
Ham, Jin Su,Park, Bohyun,Son, Mina,Roque, Jose B.,Jurczyk, Justin,Yeung, Charles S.,Baik, Mu-Hyun,Sarpong, Richmond
supporting information, p. 13041 - 13050 (2020/09/01)
Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp2)-C(sp3) bond in α-hydroxy-β-lactams using a Rh-complex leads to α-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand.
Photocyclization of α-keto amides in homogeneous solution and aqueous cyclodextrin media. The role of zwitterions and diradicals in photoinduced electron transfer reactions
Chesta, Carlos A.,Whitten, David G.
, p. 2188 - 2197 (2007/10/02)
A mechanistic investigation of the photoreaction of the N,N-disubstituted benzoyl amides, PhCOCONR'R" 1-4 (1: R' = C2H5, R" = Ph; 2: R' = R" = C2H5; 3: R' = R" = CH2Ph; 4: R' = R" = i-C3Hs
