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Diastereoselective Cyclization of 1,5‐Dienes with the C−H Bond of Pyridine Catalyzed by a Cationic Mono(phosphinoamide) Alkyl Scandium Complex
Author(s) -
Chen Yanhui,
Song Di,
Li Jing,
Hu Xiaoyan,
Bi Xianjia,
Jiang Tao,
Hou Zhaomin
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700980
Subject(s) - chemistry , cyclopentane , scandium , catalysis , pyridine , annulation , bicyclic molecule , medicinal chemistry , cationic polymerization , alkyl , conjugated system , organic chemistry , polymer
The carbocyclization of non‐conjugated dienes mediated by organometallics is an important reaction for the synthesis of a variety of carbocyclic derivatives, but the direct annulation of dienes with an inert C−H bond of a substrate has remained unexplored to date. We herein report a series of novel rare‐earth dialkyl complexes bearing a phosphinoamide anion and demonstrate that the combination of a mono(phosphinoamido)‐ligated scandium dialkyl complex with B(C 6 F 5 ) 3 results in an excellent catalyst for the cis ‐selective cyclization of 1,5‐dienes with the ortho ‐C(sp 2 )−H bond of pyridines to afford a new family of pyridyl‐functionalized 1,3‐disubstituted cyclopentane derivatives containing monocyclic, bicyclic, spirocyclic, and heterocyclic skeletons in moderate to excellent yields with high diastereoselectivities ( cis / trans up to 99:1).