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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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
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Alcohols
Asymmetry
Halogens
Iodine
Phosphates
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cited_by cdi_FETCH-LOGICAL-c422t-5549699663cd51502147be2c0dc1b760b3c8b0af5c38ff923003c56a42c6e443
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container_end_page 6990
container_issue 12
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container_title Chemical science (Cambridge)
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creator Shen, Zhigao
Pan, Xixian
Lai, Yisheng
Hu, Jiadong
Wan, Xiaolong
Li, Xiaoge
Zhang, Hui
Xie, Weiqing
description 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.
doi_str_mv 10.1039/c5sc02485d
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subjects Alcohols
Asymmetry
Halogens
Iodine
Phosphates
title Chiral ion-pair organocatalyst promotes highly enantioselective 3- exo iodo-cycloetherification of allyl alcohols
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