Issue 10, 2009
From the journal:

Organic & Biomolecular Chemistry

A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes†

Bo Jiang,ab   Wen-Juan Hao,b   Jin-Peng Zhang,c   Shu-Jiang Tu*ab  and  Feng Shib  

* Corresponding authors

a College of Chemistry, Chemical Engineering, and Materials Science, Suzhou University, Suzhou, P. R. China
E-mail: laotu@xznu.edu.cn
Fax: +86(516) 83500065
Tel: +86(516) 83500065

b School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu, P. R. China

c Department of Public Health, Xuzhou Medical College, Xuzhou 221000, People's Republic of China

Abstract

A new domino autocatalytic reaction of imines with Meldrum's acid was described. In this reaction, a series of polycyclic spiro[5.5]undecane-1,5,9-trione and dispiro[4.2.5.2]pentadecane-9,13-dione derivatives, with remarkable diastereoselectivity, were successfully synthesized in acidic condition, and up to six new bonds were formed accompanied by the C[double bond, length as m-dash]N bond cleavage of the imines and the decomposition of Meldrum's acid, with by-product of acetohydrazide as a novel autocatalyst.

Graphical abstract: A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes

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Article information

DOI
https://doi.org/10.1039/B822645H
Article type
Paper
Submitted
17 Dec 2008
Accepted
13 Mar 2009
First published
03 Apr 2009

Org. Biomol. Chem., 2009,7, 2195-2201

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A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes

B. Jiang, W. Hao, J. Zhang, S. Tu and F. Shi, Org. Biomol. Chem., 2009, 7, 2195 DOI: 10.1039/B822645H

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