Asymmetric formal [1 + 2 + 2]-cycloaddition of diazoamides with enamines and carbonyl compounds

Shanliang Dong, Minghan Yao, Yunzhe Wang, Xiongda Xie, Xinyu Jiang and Xinfang Xu ()
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Shanliang Dong: Zhejiang Sci-Tech University, School of Chemistry and Chemical Engineering
Minghan Yao: Sun Yat-sen University, School of Pharmaceutical Sciences
Yunzhe Wang: Sun Yat-sen University, School of Pharmaceutical Sciences
Xiongda Xie: Sun Yat-sen University, School of Pharmaceutical Sciences
Xinyu Jiang: Sun Yat-sen University, School of Pharmaceutical Sciences
Xinfang Xu: Zhejiang Sci-Tech University, School of Chemistry and Chemical Engineering

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract Cycloaddition reaction offers an ideal and powerful method for the construction of cyclic structures with molecular complexity and diversity. The exploration of versatile synthons, especially in situ formed species, for the assembly of poly-functionalized heterocycles in one-pot is an intriguing and challenging area in synthetic chemistry from the perspective of atom economy and bond formation efficiency. Herein, we report an asymmetric formal [1 + 2 + 2]-cycloaddition of readily accessible diazoamides with enamines and carbonyl compounds. This cascade reaction involves a 1,3-dipolar cycloaddition of ketones/aldehydes with the key zwitterionic intermediate that generated in situ through an intermolecular metal carbene transfer to nucleophilic enamines, which offers a direct access to spiro-tetrahydrofurans containing four consecutive stereocenters in high yields and excellent enantioselectivity through chiral copper complex or chiral dirhodium carboxylates catalysis.

Date: 2025
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DOI: 10.1038/s41467-025-65612-3

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