Divergent Access to Chiral C2- and C3-Alkylated Pyrrolidines by Catalyst-Tuned Regio- and Enantioselective C(sp³)-C(sp³) Coupling

Xuchao Wang, Jing Xue and Zi-Qiang Rong*

*Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi'an, Shaanxi 710072, China, Email: iamzqrongnwpu.edu.cn

X. Wang, J. Xue, Z.-Q. Rong, J. Am. Chem. Soc., 2023, 145, 15456-15464.

DOI: 10.1021/jacs.3c03900

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Abstract

Highly efficient catalyst-tuned regio- and enantioselective hydroalkylation reactions of readily available 3-pyrrolines provide chiral C2-alkylated pyrrolidines in the presence of a Co catalyst and C3-alkylated pyrrolidines in the presence of a Ni catalyst. These divergent methods use readily available catalysts, chiral BOX ligands, and reagents.

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proposed mechanisms

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Key Words

pyrrolidines, dimethoxymethylsilane

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ID: J48-Y2023