Issue 12, 2015
From the journal:

Chemical Science

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

Zhigao Shen,‡ab   Xixian Pan,‡c   Yisheng Lai,‡b   Jiadong Hu,b   Xiaolong Wan,d   Xiaoge Li,d   Hui Zhange  and  Weiqing Xie*a  

* Corresponding authors

a Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, 22 Xinong Road, Yangling 712100, China
E-mail: xiewqsioc@aliyun.com

b State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Center of Drug Discovery, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China

c Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Normal University, China

d Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China

e School of Science & Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, China

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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Article information

DOI
https://doi.org/10.1039/C5SC02485D
Article type
Edge Article
Submitted
09 Jul 2015
Accepted
26 Aug 2015
First published
27 Aug 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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