1116366-19-8Relevant academic research and scientific papers
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
, 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.
Synthesis of functionalized epoxides by copper-catalyzed alkylative epoxidation of allylic alcohols with alkyl nitriles
Bunescu, Ala,Wang, Qian,Zhu, Jieping
supporting information, p. 1890 - 1893 (2015/04/27)
A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp3)-O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted epoxides via formation of a C(sp3)-C(sp3) and a C(sp3)-O bond with moderate to excellent diastereoselectivity.
