Issue 10, 2012
From the journal:

Chemical Science

Allenoate-derived 1,5-, 1,7-, and 1,9-zwitterions as highly versatile coupling-partners for phosphine-triggered cycloaddition reactions†

Wei Meng,a   Hai-Tao Zhao,a   Jing Nie,a   Yan Zheng,a   Aiping Fuc  and  Jun-An Ma*ab  

* Corresponding authors

a Department of Chemistry, Tianjin University, Tianjin 300072, China
E-mail: majun_an68@tju.edu.cn
Fax: +86 22-2740-3475

b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry (CAS), Shanghai 200032, China

c Laboratory of New Fiber Materials and Modern Textile, Growing Base for State Key Laboratory, Qingdao University, Qingdao 266071, China

Abstract

Our computational and experimental studies show that the high order 1,n-zwitterionic intermediates (n = 5, 7 and 9) of allenoate-PR3 are real species. The cycloaddition reactions of these versatile intermediates with electrophilic-coupling partners provide novel and highly convergent synthetic approaches to medium- and large-ring compounds.

Graphical abstract: Allenoate-derived 1,5-, 1,7-, and 1,9-zwitterions as highly versatile coupling-partners for phosphine-triggered cycloaddition reactions

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Article information

DOI
https://doi.org/10.1039/C2SC20805A
Article type
Edge Article
Submitted
04 Feb 2012
Accepted
12 Jul 2012
First published
12 Jul 2012

Chem. Sci., 2012,3, 3053-3057

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Allenoate-derived 1,5-, 1,7-, and 1,9-zwitterions as highly versatile coupling-partners for phosphine-triggered cycloaddition reactions

W. Meng, H. Zhao, J. Nie, Y. Zheng, A. Fu and J. Ma, Chem. Sci., 2012, 3, 3053 DOI: 10.1039/C2SC20805A

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