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Issue 12, 2015
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Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols

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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.

Graphical abstract: Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols

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Publication details

The article was received on 09 Jul 2015, accepted on 26 Aug 2015 and first published on 27 Aug 2015


Article type: Edge Article
DOI: 10.1039/C5SC02485D
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Citation: Chem. Sci., 2015,6, 6986-6990
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    Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols

    Z. Shen, X. Pan, Y. Lai, J. Hu, X. Wan, X. Li, H. Zhang and W. Xie, Chem. Sci., 2015, 6, 6986
    DOI: 10.1039/C5SC02485D

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