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Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides.
Angew Chem Int Ed Engl. 2022 Oct 24; 61(43):e202210637.AC

Abstract

Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O-heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst-controlled highly enantioselective reaction of carbonyl ylides from metal carbenes is extremely challenging. Herein, we report a novel copper-catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides. Importantly, this protocol not only represents the first example of successful asymmetric epoxidation via carbonyl ylides, but also constitutes the first reaction of vinyl cations with carbonyl compounds. This method leads to the divergent, practical and atom-economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities via remote-stereocontrol strategy.

Authors+Show Affiliations

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China. School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, Jiaojiang, 318000, Zhejiang, China.State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35975959

Citation

Qi, Lin-Jun, et al. "Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes With Ketones Via Carbonyl Ylides." Angewandte Chemie (International Ed. in English), vol. 61, no. 43, 2022, pp. e202210637.
Qi LJ, Li CT, Huang ZQ, et al. Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides. Angew Chem Int Ed Engl. 2022;61(43):e202210637.
Qi, L. J., Li, C. T., Huang, Z. Q., Jiang, J. T., Zhu, X. Q., Lu, X., & Ye, L. W. (2022). Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides. Angewandte Chemie (International Ed. in English), 61(43), e202210637. https://doi.org/10.1002/anie.202210637
Qi LJ, et al. Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes With Ketones Via Carbonyl Ylides. Angew Chem Int Ed Engl. 2022 Oct 24;61(43):e202210637. PubMed PMID: 35975959.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides. AU - Qi,Lin-Jun, AU - Li,Cui-Ting, AU - Huang,Zheng-Qi, AU - Jiang,Jia-Tian, AU - Zhu,Xin-Qi, AU - Lu,Xin, AU - Ye,Long-Wu, Y1 - 2022/08/30/ PY - 2022/07/20/received PY - 2022/8/18/pubmed PY - 2022/8/18/medline PY - 2022/8/17/entrez KW - Alkynes KW - Annulation KW - Asymmetric Catalysis KW - Carbonyl Ylides KW - Heterocycles SP - e202210637 EP - e202210637 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 61 IS - 43 N2 - Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O-heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst-controlled highly enantioselective reaction of carbonyl ylides from metal carbenes is extremely challenging. Herein, we report a novel copper-catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides. Importantly, this protocol not only represents the first example of successful asymmetric epoxidation via carbonyl ylides, but also constitutes the first reaction of vinyl cations with carbonyl compounds. This method leads to the divergent, practical and atom-economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities via remote-stereocontrol strategy. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/35975959/Enantioselective_Copper_Catalyzed_Formal_[2+1]_and_[4+1]_Annulations_of_Diynes_with_Ketones_via_Carbonyl_Ylides_ L2 - https://doi.org/10.1002/anie.202210637 DB - PRIME DP - Unbound Medicine ER -
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