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Enantioselective Reductive N-Cyclization-Alkylation Reaction of Alkene-Tethered Oxime Esters and Alkyl Iodides by Nickel Catalysis

Xue-Gong Jia, Qi-Wei Yao and Xing-Zhong Shu*

*College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China, Email: shuxingzhlzu.edu.cn

X.-G. Jia, Q.-W. Yao, X.-Z. Shu, J. Am. Chem. Soc., 2022, 144, 13461-13467.

DOI: 10.1021/jacs.2c05523


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Abstract

Asymmetric cross-electrophile difunctionalization of tethered alkenes is a powerful tool for the production of chiral cyclic scaffolds. An enantioselective aza-Heck cyclization/cross-coupling sequence proceeds with primary, secondary, and a few tertiary alkyl iodides, to provide highly enantioenriched pyrrolines with improved molecular diversity under mild conditions.

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proposed mechanism



Key Words

1-pyrrolines, zinc


ID: J48-Y2022