Nickel-Catalyzed Enantioselective α‑Alkenylation of N‑Sulfonyl Amines: Modular Access to Chiral α‑Branched Amines

Chiral α-branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economica...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2021-03, Vol.143 (11), p.4154-4161
Main Authors: Li, Lun, Liu, Yu-Cheng, Shi, Hang
Format: Article
Language:English
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Summary:Chiral α-branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economical, modular method for a nickel-catalyzed enantioselective α-alkenylation of readily available linear N-sulfonyl amines with alkynes to afford a wide variety of allylic amines without the need for exogenous oxidants, reductants, or activating reagents. The method provides a platform for constructing chiral α-branched amines as well as derivatives such as α-amino amides and β-amino alcohols, which can be conveniently accessed from the newly introduced alkene. Given the generality, versatility, and high atom economy of this method, we anticipate that it will have broad synthetic utility.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c00622