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Molecules 2015, 20(12), 21103-21124; doi:10.3390/molecules201219748

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
Received: 5 October 2015 / Revised: 17 November 2015 / Accepted: 19 November 2015 / Published: 27 November 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [6880 KB, uploaded 27 November 2015]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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