Issue 40, 2010

Highly stereoselective synthesis of indanes with four stereogenic centers via sequential Michael reaction and [3+2] cycloaddition

Abstract

A highly efficient organocatalytic sequential reaction involving Michael addition of bis(phenylsulfonyl)ethylene, in situ condensation and intramolecular nitrone [3+2] cycloaddition with a variety of aldehydes and hydroxyamines to afford a single diastereomer of indanes with four stereogenic centers in excellent yields and stereoselectivities was developed.

Graphical abstract: Highly stereoselective synthesis of indanes with four stereogenic centers via sequential Michael reaction and [3+2] cycloaddition

Supplementary files

Article information

Article type
Communication
Submitted
25 May 2010
Accepted
25 Aug 2010
First published
14 Sep 2010

Chem. Commun., 2010,46, 7611-7613

Highly stereoselective synthesis of indanes with four stereogenic centers via sequential Michael reaction and [3+2] cycloaddition

P. J. Chua, B. Tan, L. Yang, X. Zeng, D. Zhu and G. Zhong, Chem. Commun., 2010, 46, 7611 DOI: 10.1039/C0CC01577F

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