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Pd-Catalyzed Asymmetric 5-exo-trig Cyclization/Cyclopropanation/Carbonylation of 1,6-Enynes for the Construction of Chiral 3-Azabicyclo[3.1.0]hexanes |
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| Authors: | Qiuyu Li Yunchu Zhang Pengyun Liu Jing Zhong Baihui Gong Prof. Dr. Hequan Yao Prof. Dr. Aijun Lin |
| Affiliation: | 1. State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 210009 P. R. China These authors contributed equally to this work.;2. State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 210009 P. R. China |
| Abstract: | We herein disclose a mild and efficient access to chiral 3-azabicyclo[3.1.0]hexanes via a Pd-catalyzed asymmetric 5-exo-trig cyclization/cyclopropanation/carbonylation of 1,6-enynes. Various nucleophiles, such as alcohols, phenols, amines and water, are well compatible with the reaction system. This reaction forms three C−C bonds, two rings, two adjacent quaternary carbon stereocenters as well as one C−O/C−N bond with excellent regio- and enantioselectivities. The products could be further functionalized to generate a library of 3-azabicyclo[3.1.0]hexane frameworks. |
| Keywords: | 3-Azabicyclo[3.1.0]Hexanes Carbonylation Cyclopropanation Palladium Catalysis Quaternary Carbon Stereocenter |