89619-10-3Relevant articles and documents
Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols
Capel, Estefania,Rodríguez-Rodríguez, Marta,Uria, Uxue,Pedron, Manuel,Tejero, Tomas,Vicario, Jose L.,Merino, Pedro
supporting information, p. 693 - 707 (2022/01/04)
The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with N-bromosuccinimide has been experimentally and computationally studied. The reaction yields highly enantioenriched cyclopenta
Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process
Cao, Weidi,Dai, Li,Feng, Xiaoming,Hu, Xinyue,Liu, Wen,Zeng, Zi,Zhou, Yuqiao
supporting information, p. 26599 - 26603 (2021/11/16)
A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N′-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.
Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters
Kang, Jun-Chen,Tu, Yong-Qiang,Dong, Jia-Wei,Chen, Chao,Zhou, Jia,Ding, Tong-Mei,Zai, Jian-Tao,Chen, Zhi-Min,Zhang, Shu-Yu
supporting information, p. 2536 - 2540 (2019/04/30)
The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This strategy provides a facile, direct, and complementary approach to construct all-carbon quaternary stereocenters. In addition, the reaction has the advantages of being chemical oxidant-free and metal-free and has safe and mild reaction conditions.