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A One-Pot Approach to 2‑Substituted-2-(Dimethoxyphosphoryl)-Pyrrolidines from Substituted tert-Butyl 4‑Oxobutylcarbamates and Trimethyl Phosphite

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journal contribution
posted on 03.09.2021, 08:04 by Zhao-Dan Chen, Wen-Ke Xu, Jia-Ming Guo, Ling Chen, Bang-Guo Wei, Chang-Mei Si, Guo-Qiang Lin
A novel approach to 2-substituted-2-(dimethoxyphosphoryl)-pyrrolidines 7a7o and 9a9r has been developed, which features a TMSOTf-mediated one-pot intramolecular cyclization and phosphonylation of substituted tert-butyl 4-oxobutylcarbamates. The major advantages of this method include simple operation under mild reaction conditions, the use of cheap Lewis acid, and good to excellent yields with high diastereoselectivities (dr up to 99:1).