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Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction.
Org Lett. 2020 02 21; 22(4):1589-1593.OL

Abstract

The spiroindoline skeleton featured with 2,7-diazaspiro[4.4]nonane exists in various structurally intricate and biologically active monoterpene indole alkaloids. A catalytic asymmetric cascade enamine isomerization/spirocyclization/dearomatization succession to construct the spiroindoline was developed, which employed the indolyl dihydropyridine as a substrate under catalysis of the chiral phosphoric acid. This cascade reaction provided various spiroindolines in both diastereoselective and enantionselective fashions.

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Authors+Show Affiliations

Pan Z
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Liu Y
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Hu F
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Liu Q
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Shang W
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Ji X
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Xia C
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

31990194

Citation

Pan, Zhiqiang, et al. "Enantioselective Synthesis of Spiroindolines Via Cascade Isomerization/Spirocyclization/Dearomatization Reaction." Organic Letters, vol. 22, no. 4, 2020, pp. 1589-1593.
Pan Z, Liu Y, Hu F, et al. Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction. Org Lett. 2020;22(4):1589-1593.
Pan, Z., Liu, Y., Hu, F., Liu, Q., Shang, W., Ji, X., & Xia, C. (2020). Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction. Organic Letters, 22(4), 1589-1593. https://doi.org/10.1021/acs.orglett.0c00181
Pan Z, et al. Enantioselective Synthesis of Spiroindolines Via Cascade Isomerization/Spirocyclization/Dearomatization Reaction. Org Lett. 2020 02 21;22(4):1589-1593. PubMed PMID: 31990194.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction. AU - Pan,Zhiqiang, AU - Liu,Yuchang, AU - Hu,Fengchi, AU - Liu,Qinglong, AU - Shang,Wenbin, AU - Ji,Xu, AU - Xia,Chengfeng, Y1 - 2020/01/28/ PY - 2020/1/29/pubmed PY - 2020/1/29/medline PY - 2020/1/29/entrez SP - 1589 EP - 1593 JF - Organic letters JO - Org Lett VL - 22 IS - 4 N2 - The spiroindoline skeleton featured with 2,7-diazaspiro[4.4]nonane exists in various structurally intricate and biologically active monoterpene indole alkaloids. A catalytic asymmetric cascade enamine isomerization/spirocyclization/dearomatization succession to construct the spiroindoline was developed, which employed the indolyl dihydropyridine as a substrate under catalysis of the chiral phosphoric acid. This cascade reaction provided various spiroindolines in both diastereoselective and enantionselective fashions. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31990194/Enantioselective_Synthesis_of_Spiroindolines_via_Cascade_Isomerization/Spirocyclization/Dearomatization_Reaction_ DB - PRIME DP - Unbound Medicine ER -