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

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-cycloetherifica...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2015-01, Vol.6 (12), p.6986-6990
Main Authors: Shen, Zhigao, Pan, Xixian, Lai, Yisheng, Hu, Jiadong, Wan, Xiaolong, Li, Xiaoge, Zhang, Hui, Xie, Weiqing
Format: Article
Language:English
Subjects:
Alcohols
Asymmetry
Halogens
Iodine
Phosphates
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc02485d