Tags

Type your tag names separated by a space and hit enter

Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence.
Angew Chem Int Ed Engl. 2018 03 01; 57(10):2653-2656.AC

Abstract

A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

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.
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.
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.
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

29327453

Citation

Xia, Zi-Lei, et al. "Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines Through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence." Angewandte Chemie (International Ed. in English), vol. 57, no. 10, 2018, pp. 2653-2656.
Xia ZL, Zheng C, Wang SG, et al. Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence. Angew Chem Int Ed Engl. 2018;57(10):2653-2656.
Xia, Z. L., Zheng, C., Wang, S. G., & You, S. L. (2018). Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence. Angewandte Chemie (International Ed. in English), 57(10), 2653-2656. https://doi.org/10.1002/anie.201712435
Xia ZL, et al. Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines Through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence. Angew Chem Int Ed Engl. 2018 03 1;57(10):2653-2656. PubMed PMID: 29327453.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence. AU - Xia,Zi-Lei, AU - Zheng,Chao, AU - Wang,Shou-Guo, AU - You,Shu-Li, Y1 - 2018/02/06/ PY - 2017/12/04/received PY - 2018/1/13/pubmed PY - 2018/1/13/medline PY - 2018/1/13/entrez KW - asymmetric catalysis KW - chiral phosphoric acid KW - dearomatization KW - spiroindolines KW - transfer hydrogenation SP - 2653 EP - 2656 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 57 IS - 10 N2 - A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/29327453/Catalytic_Asymmetric_Dearomatization_of_Indolyl_Dihydropyridines_through_an_Enamine_Isomerization/Spirocyclization/Transfer_Hydrogenation_Sequence_ DB - PRIME DP - Unbound Medicine ER -
Grapherence [↓6]
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.