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Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles.
Angew Chem Int Ed Engl. 2022 Feb 07; 61(7):e202115554.AC

Abstract

Here, we report a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement via a non-diazo approach, leading to the practical and atom-economic assembly of various valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon stereocenter in generally moderate to good yields with wide substrate scope and excellent enantioselectivities (up to 99 % ee). Importantly, this protocol not only represents the first example of catalytic asymmetric [1,2]-Stevens-type rearrangement based on alkynes but also constitutes the first asymmetric formal carbene insertion into the Si-O bond.

Authors+Show Affiliations

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and 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, and 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, and 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, and 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, and 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, and 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, and 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

34904775

Citation

Hong, Feng-Lin, et al. "Copper-Catalyzed Asymmetric Diyne Cyclization Via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles." Angewandte Chemie (International Ed. in English), vol. 61, no. 7, 2022, pp. e202115554.
Hong FL, Shi CY, Hong P, et al. Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles. Angew Chem Int Ed Engl. 2022;61(7):e202115554.
Hong, F. L., Shi, C. Y., Hong, P., Zhai, T. Y., Zhu, X. Q., Lu, X., & Ye, L. W. (2022). Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles. Angewandte Chemie (International Ed. in English), 61(7), e202115554. https://doi.org/10.1002/anie.202115554
Hong FL, et al. Copper-Catalyzed Asymmetric Diyne Cyclization Via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles. Angew Chem Int Ed Engl. 2022 Feb 7;61(7):e202115554. PubMed PMID: 34904775.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles. AU - Hong,Feng-Lin, AU - Shi,Chong-Yang, AU - Hong,Pan, AU - Zhai,Tong-Yi, AU - Zhu,Xin-Qi, AU - Lu,Xin, AU - Ye,Long-Wu, Y1 - 2021/12/23/ PY - 2021/11/15/received PY - 2021/12/15/pubmed PY - 2021/12/15/medline PY - 2021/12/14/entrez KW - Alkynes KW - Asymmetric catalysis KW - Heterocycles KW - Metal carbenes KW - Rearrangement SP - e202115554 EP - e202115554 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 61 IS - 7 N2 - Here, we report a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement via a non-diazo approach, leading to the practical and atom-economic assembly of various valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon stereocenter in generally moderate to good yields with wide substrate scope and excellent enantioselectivities (up to 99 % ee). Importantly, this protocol not only represents the first example of catalytic asymmetric [1,2]-Stevens-type rearrangement based on alkynes but also constitutes the first asymmetric formal carbene insertion into the Si-O bond. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/34904775/Copper_Catalyzed_Asymmetric_Diyne_Cyclization_via_[12]_Stevens_Type_Rearrangement_for_the_Synthesis_of_Chiral_Chromeno[34_c]pyrroles_ L2 - https://doi.org/10.1002/anie.202115554 DB - PRIME DP - Unbound Medicine ER -
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