Tan, Yun-Xuan published the artcileAn unconventional trans-exo-selective cyclization of alkyne-tethered cyclohexadienones initiated by rhodium(III)-catalyzed C-H activation via insertion relay, Application In Synthesis of 637-07-0, the publication is CCS Chemistry (2021), 3(5), 1582-1595, database is CAplus.
Different from the established trans-endo-selective cyclization of alkyne-tethered electrophiles that involve an E/Z isomerization process, herein, the authors present a novel strategy to allow trans-exo-selective arylative cyclization of 1,6-enynes. Through initiation of rhodium(III)-catalyzed C-H activation, a diverse range of N-heterocyclic directing groups, including pyridine, pyrazole, imidazo[1,2-a] pyridine, benzoxazole, benzothiazole, and purine, was feasible for the cascade transformation, exhibiting high efficiency (up to 92% yield), broad substrate scope, and excellent functional group compatibility. Moreover, the modification of natural products and pharmaceutical compounds was also demonstrated to showcase its synthetic utility. Based on d. functional theory (DFT) calculations, a key three-membered ring intermediate through the insertion relay, rather than the direct E/Z isomerization of alkenyl rhodium species, controlled the stereochem. outcome for this trans-exo-selective cyclization. The subsequent ring-opening protonation of the more favored rotamer led to exclusive trans-exo-selectivity.
CCS Chemistry published new progress about 637-07-0. 637-07-0 belongs to chlorides-buliding-blocks, auxiliary class Inhibitor,Cell Cycle,PPAR, name is Ethyl 2-(4-chlorophenoxy)-2-methylpropanoate, and the molecular formula is C11H14O2, Application In Synthesis of 637-07-0.
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