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Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates.
Angew Chem Int Ed Engl. 2015 Nov 16; 54(47):14146-9.AC

Abstract

The highly efficient synthesis of the enantioenriched spiroindolines by iridium-catalyzed asymmetric allylic dearomatization and reduction is presented. Spiroindolines containing three contiguous stereogenic centers were obtained with excellent diastereo- and enantioselectivity. In addition, a chiral tryptamine derivative could be easily accessed in good yield with excellent ee value through an unprecedented dearomatization/retro-Mannich/hydrolysis cascade reaction of an indole derivative.

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Authors+Show Affiliations

Zhuo CX
State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Zhou Y
State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Cheng Q
State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Huang L
State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
You SL
State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/. slyou@sioc.ac.cn. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China). slyou@sioc.ac.cn.

Pub Type(s)

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

Language

eng

PubMed ID

26403164

Citation

Zhuo, Chun-Xiang, et al. "Enantioselective Construction of Spiroindolines With Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives Via Reactive Spiroindolenine Intermediates." Angewandte Chemie (International Ed. in English), vol. 54, no. 47, 2015, pp. 14146-9.
Zhuo CX, Zhou Y, Cheng Q, et al. Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates. Angew Chem Int Ed Engl. 2015;54(47):14146-9.
Zhuo, C. X., Zhou, Y., Cheng, Q., Huang, L., & You, S. L. (2015). Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates. Angewandte Chemie (International Ed. in English), 54(47), 14146-9. https://doi.org/10.1002/anie.201507193
Zhuo CX, et al. Enantioselective Construction of Spiroindolines With Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives Via Reactive Spiroindolenine Intermediates. Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14146-9. PubMed PMID: 26403164.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates. AU - Zhuo,Chun-Xiang, AU - Zhou,Yong, AU - Cheng,Qiang, AU - Huang,Lin, AU - You,Shu-Li, Y1 - 2015/09/25/ PY - 2015/08/02/received PY - 2015/9/26/entrez PY - 2015/9/26/pubmed PY - 2015/9/26/medline KW - asymmetric catalysis KW - dearomatization KW - heterocycles KW - iridium KW - synthetic methods SP - 14146 EP - 9 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 47 N2 - The highly efficient synthesis of the enantioenriched spiroindolines by iridium-catalyzed asymmetric allylic dearomatization and reduction is presented. Spiroindolines containing three contiguous stereogenic centers were obtained with excellent diastereo- and enantioselectivity. In addition, a chiral tryptamine derivative could be easily accessed in good yield with excellent ee value through an unprecedented dearomatization/retro-Mannich/hydrolysis cascade reaction of an indole derivative. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/26403164/Enantioselective_Construction_of_Spiroindolines_with_Three_Contiguous_Stereogenic_Centers_and_Chiral_Tryptamine_Derivatives_via_Reactive_Spiroindolenine_Intermediates_ DB - PRIME DP - Unbound Medicine ER -