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Abstract [3+n]‐Cycloaddition reactions that employ donor‐acceptor cyclopropanes using either chiral catalysts and racemic cyclopropanes or achiral catalysts and chiral, non‐racemic, cyclopropanes have become useful transformations for the construction of carbocyclic and heterocyclic compounds, with both processes offering mechanistic and structural advantages in ring formation. Although the vast majority of asymmetric cycloaddition reactions of donor‐acceptor cyclopropanes have been performed with racemic cyclopropane compounds catalyzed by Lewis acids with chiral ligands, optically active cyclopropane compounds can serve the same role using Lewis acids without chiral ligands. This review covers the use of chiral catalysts with racemic donor‐acceptor cyclopropanes and the use of chiral non‐racemic donor‐acceptor cyclopropanes with achiral Lewis acid catalysts.
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Copper-Catalyzed 1,3-Aminocyclization of Cyclopropanes as a Rapid Entry to γ-Amino Heterocycles
We herein report a copper-catalyzed 1,3-aminocyclization of cyclopropanes as a direct and versatile entry into important heterocycles. This reaction was initiated by a copper-catalyzed, NFSI-promoted ring opening of cyclopropanes, followed by nucleophilic cyclization. A variety of nucleophiles successfully participate in this transformation, including alcohols, carboxylic acids, sulfonamides, and amides, for the construction of diverse cyclic ethers, pyrrolidines, lactones, and iminolactones.
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- Award ID(s):
- 2154501
- PAR ID:
- 10647816
- Publisher / Repository:
- ACS Publications
- Date Published:
- Journal Name:
- Organic Letters
- Volume:
- 26
- Issue:
- 44
- ISSN:
- 1523-7060
- Page Range / eLocation ID:
- 9508 to 9512
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1021/acs.orglett.4c03475
