3 years ago

Diastereoselective Cyclization of 1,5-Dienes with the C−H Bond of Pyridine Catalyzed by a Cationic Mono(phosphinoamide) Alkyl Scandium Complex

Diastereoselective Cyclization of 1,5-Dienes with the C−H Bond of Pyridine Catalyzed by a Cationic Mono(phosphinoamide) Alkyl Scandium Complex
Xiaoyan Hu, Tao Jiang, Zhaomin Hou, Yanhui Chen, Jing Li, Di Song, Xianjia Bi
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(C6F5)3 results in an excellent catalyst for the cis-selective cyclization of 1,5-dienes with the ortho-C(sp2)−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). It rings true: The combination of a novel mono(phosphinoamido)-ligated scandium complex such as 2 a-Sc with a boron compound such as B(C6F5)3 results in a unique and highly efficient catalyst for the cis-selective cyclization of 1,5-dienes with the ortho-C(sp2)−H bond of pyridines. The resulting pyridyl-functionalized 1,3-disubstituted cyclopentane derivatives are obtained in excellent yields with high diastereoselectivities.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/cctc.201700980

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