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Asymmetric Synthesis of Pyrrolidines via Oxetane Desymmetrization

Renwei Zhang, Meng Sun, Qiaolin Yan, Xingbang Lin, Xin Li, Xin Fang, Herman H. Y. Sung, Ian D. Williams and Jianwei Sun*

*The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR, China, Email: sunjwust.hk

R. Zhang, M. Sun, Q. Yan, X. Lin, X. Li, X. Fang, H. H. Y. Sung, J. D. Williams, J. Sun, Org. Lett., 2022, 24, 2359-2364.

DOI: 10.1021/acs.orglett.2c00564



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Abstract

Oxetane desymmetrization enables an asymmetric synthesis of chiral pyrrolidines bearing an all-carbon quaternary stereocenter in the 3-position either using a readily available tert-butylsulfinamide chiral auxiliary or a catalytic system with a chiral phosphoric acid as the source of chirality.

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Key Words

Pyrrolidines, Organocatalysis


ID: J54-Y2022