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Open AccessArticle

Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles

1
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China
2
School of Pharmaceutical Sciences, Gannan Medical University, Yi Xue Yuan Road, Ganzhou 341000, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(12), 21103-21124; https://doi.org/10.3390/molecules201219748
Received: 5 October 2015 / Revised: 17 November 2015 / Accepted: 19 November 2015 / Published: 27 November 2015
(This article belongs to the Section Organic Chemistry)
Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i. View Full-Text
Keywords: iridium catalyst; asymmetric ring-opening; oxabenzonorbornadiene; chiral bisphosphine ligand; N-substituted piperazines iridium catalyst; asymmetric ring-opening; oxabenzonorbornadiene; chiral bisphosphine ligand; N-substituted piperazines
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Yang, W.; Luo, R.; Yang, D. Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles. Molecules 2015, 20, 21103-21124.

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