131433-15-3Relevant 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
, p. 13041 - 13050 (2020)
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.
HIGHLY SELECTIVE PHOTOREACTIONS OF α-OXOAMIDES AND α-TROPOLONE ALKYL ETHERS IN CRYSTALLINE INCLUSION COMPLEXES
Toda, Fumio,Tanaka, Koichi,Yagi, Minoru
, p. 1495 - 1502 (2007/10/02)
Control of photocyclization of three α-oxoamides in crystalline inclusion complexes with three kinds of host compounds was studied.In all cases, β-lactams were obtained exclusively.In two cases, cis-β-lactams were formed selectively.By an enantioselective
