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Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles.
Angew Chem Int Ed Engl. 2017 02 01; 56(6):1530-1534.AC

Abstract

An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of benzoxazoles, benzothiazoles, and benzimidazoles was developed. The reaction was found to be compatible with a wide range of five-membered-ring electron-deficient heteroaromatic compounds and furnished the corresponding dearomatized heterocycles in high yield with excellent enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang ZP
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Zheng C
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Huang L
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Qian C
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
You SL
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.

MeSH

Allyl CompoundsBenzimidazolesBenzothiazolesBenzoxazolesCatalysisDrug DiscoveryIridiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

28074594

Citation

Yang, Ze-Peng, et al. "Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles." Angewandte Chemie (International Ed. in English), vol. 56, no. 6, 2017, pp. 1530-1534.
Yang ZP, Zheng C, Huang L, et al. Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles. Angew Chem Int Ed Engl. 2017;56(6):1530-1534.
Yang, Z. P., Zheng, C., Huang, L., Qian, C., & You, S. L. (2017). Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles. Angewandte Chemie (International Ed. in English), 56(6), 1530-1534. https://doi.org/10.1002/anie.201611056
Yang ZP, et al. Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles. Angew Chem Int Ed Engl. 2017 02 1;56(6):1530-1534. PubMed PMID: 28074594.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles. AU - Yang,Ze-Peng, AU - Zheng,Chao, AU - Huang,Lin, AU - Qian,Chao, AU - You,Shu-Li, Y1 - 2017/01/11/ PY - 2016/11/11/received PY - 2017/1/12/pubmed PY - 2019/1/24/medline PY - 2017/1/12/entrez KW - asymmetric catalysis KW - dearomatization KW - drug discovery KW - heterocycles KW - iridium SP - 1530 EP - 1534 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 6 N2 - An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of benzoxazoles, benzothiazoles, and benzimidazoles was developed. The reaction was found to be compatible with a wide range of five-membered-ring electron-deficient heteroaromatic compounds and furnished the corresponding dearomatized heterocycles in high yield with excellent enantioselectivity. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28074594/Iridium_Catalyzed_Intramolecular_Asymmetric_Allylic_Dearomatization_Reaction_of_Benzoxazoles_Benzothiazoles_and_Benzimidazoles_ DB - PRIME DP - Unbound Medicine ER -