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Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines.
Angew Chem Int Ed Engl. 2017 06 19; 56(26):7440-7443.AC

Abstract

A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet-Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee). With this method, a formal synthesis of tangutorine and a total synthesis of deplancheine were achieved in a highly efficient manner.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang SG
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Xia ZL
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Xu RQ
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Liu XJ
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Zheng C
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
You SL
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China.

Pub Type(s)

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

Language

eng

PubMed ID

28466512

Citation

Wang, Shou-Guo, et al. "Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines." Angewandte Chemie (International Ed. in English), vol. 56, no. 26, 2017, pp. 7440-7443.
Wang SG, Xia ZL, Xu RQ, et al. Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angew Chem Int Ed Engl. 2017;56(26):7440-7443.
Wang, S. G., Xia, Z. L., Xu, R. Q., Liu, X. J., Zheng, C., & You, S. L. (2017). Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angewandte Chemie (International Ed. in English), 56(26), 7440-7443. https://doi.org/10.1002/anie.201703178
Wang SG, et al. Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angew Chem Int Ed Engl. 2017 06 19;56(26):7440-7443. PubMed PMID: 28466512.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. AU - Wang,Shou-Guo, AU - Xia,Zi-Lei, AU - Xu,Ren-Qi, AU - Liu,Xi-Jia, AU - Zheng,Chao, AU - You,Shu-Li, Y1 - 2017/05/23/ PY - 2017/03/27/received PY - 2017/5/4/pubmed PY - 2017/5/4/medline PY - 2017/5/4/entrez KW - alkaloids KW - asymmetric catalysis KW - heterocycles KW - organocatalysis KW - total synthesis SP - 7440 EP - 7443 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 26 N2 - A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet-Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee). With this method, a formal synthesis of tangutorine and a total synthesis of deplancheine were achieved in a highly efficient manner. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28466512/Construction_of_Chiral_Tetrahydro_β_Carbolines:_Asymmetric_Pictet_Spengler_Reaction_of_Indolyl_Dihydropyridines_ L2 - https://doi.org/10.1002/anie.201703178 DB - PRIME DP - Unbound Medicine ER -