title: A study on the substituent effects of norbornadiene derivatives in iridium-catalyzed asymmetric [2 + 2] cycloaddition reactions.
abstract: Employing a series of norbornadiene derivatives as substrates, the effects of various substituents on the Ir-catalyzed asymmetric [2 + 2] cycloaddition reactions with arylacetylenes were studied. It was found that the atom forming the short bridge chain had a great effect on the enantioselectivity of the reaction. Heteroatoms, such as oxygen and nitrogen, always resulted in excellent enantioselectivity. However, carbon atoms could decrease the enantioselective control ability of the catalyst over the reaction. The groups on the unreacted carbon-carbon double bond were found to have but a little effect on the reaction. Based on the results of the experiments, a mechanism was also hypothesized for the reaction.
authors: Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan University of Nationalities, Kunming, 650500, China.
authors: Jun
authors: J
authors: Hu
authors: Qingjing
authors: Q
authors: Yang
authors: Lu
authors: L
authors: Yu
authors: Jianbin
authors: J
authors: Xu
authors: Shanshan
authors: S
authors: Liu
authors: Chao
authors: C
authors: Huang
authors: Lin
authors: L
authors: Wang
authors: Yongyun
authors: Y
authors: Zhou
authors: Baomin
authors: B
authors: Fan
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D009636:Norbornanes / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009636:Norbornanes; D007495:Iridium; D009584:Nitrogen; D010100:Oxygen