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Shen, Zhigao; Pan, Xixian; Lai, Yisheng; Hu, Jiadong; Wan, Xiaolong; Li, Xiaoge; Zhang, Hui; Xie, Weiqing
Chemical science (Cambridge), 01/2015, Letnik: 6, Številka: 12Journal Article
By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3- iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3- iodo-cycloetherification/Wagner-Meerwein rearrangement of allyl alcohols en route to enantioenriched 2-iodomethyl-2-aryl cycloalkanones was subsequently developed. Due to the participation of adjacent iodine, the Wagner-Meerwein rearrangement of 2-iodomethyl-2-aryl epoxide proceeds with unusual retention of stereoconfiguration.
