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Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes.
Org Lett. 2018 02 02; 20(3):880-883.OL

Abstract

Readily available phenol-derived biaryls reacted with allenes under palladium catalysis to provide a variety of highly valuable spiro[cyclohexane-1,1'-indene]-2,5-dien-4-ones. This new catalytic process, involving a key step of regioselective allylative dearomatization of phenol, proceeded efficiently through a [3 + 2] spiroannulation pathway by overcoming undesired β-hydride elimination. Preliminary asymmetric studies showed that high enantioselectivity could be realized by using a commercially available PHOX ligand. Moreover, the potential application of this method was exemplified by several further transformations.

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Authors+Show Affiliations

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710127, China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710127, China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710127, China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710127, China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710127, China.

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

29355021

Citation

Hu, Wenjie, et al. "Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes." Organic Letters, vol. 20, no. 3, 2018, pp. 880-883.

Hu W, Wang H, Bai L, et al. Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes. Org Lett. 2018;20(3):880-883.

Hu, W., Wang, H., Bai, L., Liu, J., & Luan, X. (2018). Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes. Organic Letters, 20(3), 880-883. https://doi.org/10.1021/acs.orglett.8b00014

Hu W, et al. Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes. Org Lett. 2018 02 2;20(3):880-883. PubMed PMID: 29355021.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes. AU - Hu,Wenjie, AU - Wang,Hui, AU - Bai,Lu, AU - Liu,Jingjing, AU - Luan,Xinjun, Y1 - 2018/01/22/ PY - 2018/1/23/pubmed PY - 2018/1/23/medline PY - 2018/1/23/entrez SP - 880 EP - 883 JF - Organic letters JO - Org Lett VL - 20 IS - 3 N2 - Readily available phenol-derived biaryls reacted with allenes under palladium catalysis to provide a variety of highly valuable spiro[cyclohexane-1,1'-indene]-2,5-dien-4-ones. This new catalytic process, involving a key step of regioselective allylative dearomatization of phenol, proceeded efficiently through a [3 + 2] spiroannulation pathway by overcoming undesired β-hydride elimination. Preliminary asymmetric studies showed that high enantioselectivity could be realized by using a commercially available PHOX ligand. Moreover, the potential application of this method was exemplified by several further transformations. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/29355021/Pd_0__Catalyzed_Intermolecular_Dearomatizing_[3_+_2]_Spiroannulation_of_Phenol_Based_Biaryls_and_Allenes_ DB - PRIME DP - Unbound Medicine ER -