P‑Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions

A new pair of P-stereogenic ligands with multiple chiral centers were synthesized and used in the copper­(I)-catalyzed enatioselective [3 + 2] cycloaddition of iminoesters with alkenes. A variety of highly functionalized pyrrolidines were obtained in excellent yield and enatioselectivity. This is th...

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Bibliographic Details
Published in:Organic letters 2019-04, Vol.21 (8), p.2782-2785
Main Authors: Gan, Zhenjie, Zhi, Mengna, Han, Ruiping, Li, Er-Qing, Duan, Zheng, Mathey, François
Format: Article
Language:English
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Summary:A new pair of P-stereogenic ligands with multiple chiral centers were synthesized and used in the copper­(I)-catalyzed enatioselective [3 + 2] cycloaddition of iminoesters with alkenes. A variety of highly functionalized pyrrolidines were obtained in excellent yield and enatioselectivity. This is the first example of a pair of P-stereogenic ligands working as pseudoenantiomers to tune the enantio- and diastereoselective 1,3-dipolar cycloaddition, and providing a pair of enantiomerically pure pyrrolidines, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00734