426841-80-7Relevant articles and documents
Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Organoboronic Acids
Lautens, Mark,Dockendorff, Chris,Fagnou, Keith,Malicki, Adrianna
, p. 1311 - 1314 (2002)
(Equation Presented) The first rhodium(I)-catalyzed asymmetric addition of organoboronic acids to oxabicyclic alkenes is reported. This asymmetric ring-opening (ARO) reaction can proceed in high yield under very mild conditions with electronically diverse
Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes
Tan, Yun,Yao, Yongqi,Yang, Wen,Lin, Qifu,Huang, Guobao,Tan, Minxiong,Chen, Shuqi,Chen, Donghan,Yang, Dingqiao
supporting information, p. 139 - 145 (2019/11/28)
Water-promoted palladium-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of alkoxysilanes has been developed in a one-pot fashion, yielding cis-1,2-dihydronaphthalen-1-ols in favourable yields (up to 98%) with gratifying enantioselectivities (up to 98% ee) under mild conditions. To the best of our knowledge, it represents the first example in the ring-opening reactions of oxabicyclic alkenes with alkoxysilanes. Furthermore, the cis-1,2-configuration of product was established by X-ray diffraction analysis, and a possible mechanism for the present catalytic ring-opening reaction was also proposed. (Figure presented.).
Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System
Zhang, Wei,Chen, Jingchao,Zeng, Guangzhi,Yang, Fan,Xu, Jianbin,Sun, Weiqing,Shinde, Madhuri Vikas,Fan, Baomin
, p. 2641 - 2647 (2017/03/14)
The asymmetric ring opening reactions of bicyclic alkenes with boronic acids were accomplished by using a highly active palladium/zinc co-catalytic system that was suitable for both azabenzonorbornadienes and oxabenzonorbornadienes, which were transformed to the corresponding chiral hydronaphthalene products in high yields (up to 99%) and high optical purities (up to 98% ee). The reaction protocol is general and mild and displays good functional group tolerance.