title: Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols.
abstract: A new palladium/zinc co-catalyst system associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols is reported. This catalyst system allows the formation of cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95 % yield) with excellent enantioselectivities (up to 99 % ee). The cis-configuration of the product has been confirmed by X-ray crystal structure analysis. To the best of our knowledge, it represents the first example in ring-opening reactions of bicycloalkenes with heteronucleophiles in a syn-stereoselective manner.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, Guangdong, 518055 (P. R. China).
authors.forename: Sifeng
authors.initials: S
authors.lastname: Li
authors.affiliation: YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500 (P. R. China).
authors.forename: Jianbin
authors.initials: J
authors.lastname: Xu
authors.affiliation: YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500 (P. R. China). adams.bmf@hotmail.com.|State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tinajim, 300071 (P. R. China). adams.bmf@hotmail.com.
authors.forename: Baomin
authors.initials: B
authors.lastname: Fan
authors.affiliation: YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500 (P. R. China).
authors.forename: Zhiwu
authors.initials: Z
authors.lastname: Lu
authors.affiliation: YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500 (P. R. China).
authors.forename: Chaoyuan
authors.initials: C
authors.lastname: Zeng
authors.affiliation: School of Chinese Medicine, Hong Kong Baptist University.
authors.forename: Zhaoxiang
authors.initials: Z
authors.lastname: Bian
authors.affiliation: YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500 (P. R. China).
authors.forename: Yongyun
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, Guangdong, 518055 (P. R. China). wang.j@sustc.edu.cn.
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
keywords: asymmetric catalysis; oxabenzonorbornadienes; phenols; ring-opening reaction; syn-stereoselectivity