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Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols.


ABSTRACT: By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-exo 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.

SUBMITTER: Shen Z 

PROVIDER: S-EPMC5947518 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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Chiral ion-pair organocatalyst promotes highly enantioselective 3-<i>exo</i> iodo-cycloetherification of allyl alcohols.

Shen Zhigao Z   Pan Xixian X   Lai Yisheng Y   Hu Jiadong J   Wan Xiaolong X   Li Xiaoge X   Zhang Hui H   Xie Weiqing W  

Chemical science 20150827 12


By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-<i>exo</i> iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-<i>exo</i> 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  ...[more]

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