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Enantioselective Desymmetrization of Bisphenol Derivatives via Ir-Catalyzed Allylic Dearomatization.
J Am Chem Soc. 2020 11 11; 142(45):19354-19359.JA

Abstract

Spirocyclic hexadienones with multiple stereogenic centers are frequently found in natural products but remain challenging targets to synthesize. Herein, we report the enantioselective desymmetrization of bisphenol derivatives via Ir-catalyzed allylic dearomatization reactions, affording spirocyclic hexadienone derivatives with up to three contiguous stereogenic centers in good yields (up to 90%) and excellent enantioselectivity (up to 99% ee). The high efficiency of this reaction is exemplified by the short reaction time (30 min), low catalyst loading (down to 0.2 mol %), and ability to perform the reaction on a gram-scale. The total syntheses of (+)-tatanan B and (+)-tatanan C were also realized using this Ir-catalyzed allylic dearomatization reaction as a key step.

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Authors+Show Affiliations

Wang Y
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Zhang WY
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Xie JH
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Yu ZL
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Tan JH
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, 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, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Hou XL
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, 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, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

Pub Type(s)

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

Language

eng

PubMed ID

33140959

Citation

Wang, Ye, et al. "Enantioselective Desymmetrization of Bisphenol Derivatives Via Ir-Catalyzed Allylic Dearomatization." Journal of the American Chemical Society, vol. 142, no. 45, 2020, pp. 19354-19359.
Wang Y, Zhang WY, Xie JH, et al. Enantioselective Desymmetrization of Bisphenol Derivatives via Ir-Catalyzed Allylic Dearomatization. J Am Chem Soc. 2020;142(45):19354-19359.
Wang, Y., Zhang, W. Y., Xie, J. H., Yu, Z. L., Tan, J. H., Zheng, C., Hou, X. L., & You, S. L. (2020). Enantioselective Desymmetrization of Bisphenol Derivatives via Ir-Catalyzed Allylic Dearomatization. Journal of the American Chemical Society, 142(45), 19354-19359. https://doi.org/10.1021/jacs.0c09638
Wang Y, et al. Enantioselective Desymmetrization of Bisphenol Derivatives Via Ir-Catalyzed Allylic Dearomatization. J Am Chem Soc. 2020 11 11;142(45):19354-19359. PubMed PMID: 33140959.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Desymmetrization of Bisphenol Derivatives via Ir-Catalyzed Allylic Dearomatization. AU - Wang,Ye, AU - Zhang,Wen-Yun, AU - Xie,Jia-Hao, AU - Yu,Zong-Lun, AU - Tan,Jia-Hao, AU - Zheng,Chao, AU - Hou,Xue-Long, AU - You,Shu-Li, Y1 - 2020/11/03/ PY - 2020/11/4/pubmed PY - 2020/11/4/medline PY - 2020/11/3/entrez SP - 19354 EP - 19359 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 142 IS - 45 N2 - Spirocyclic hexadienones with multiple stereogenic centers are frequently found in natural products but remain challenging targets to synthesize. Herein, we report the enantioselective desymmetrization of bisphenol derivatives via Ir-catalyzed allylic dearomatization reactions, affording spirocyclic hexadienone derivatives with up to three contiguous stereogenic centers in good yields (up to 90%) and excellent enantioselectivity (up to 99% ee). The high efficiency of this reaction is exemplified by the short reaction time (30 min), low catalyst loading (down to 0.2 mol %), and ability to perform the reaction on a gram-scale. The total syntheses of (+)-tatanan B and (+)-tatanan C were also realized using this Ir-catalyzed allylic dearomatization reaction as a key step. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/33140959/Enantioselective_Desymmetrization_of_Bisphenol_Derivatives_via_Ir_Catalyzed_Allylic_Dearomatization_ DB - PRIME DP - Unbound Medicine ER -