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Synlett 2011(7): 1005-1009  
DOI: 10.1055/s-0030-1259707
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of 3-Hydroxyindanones via N-Heterocyclic Carbene Catalyzed [4+1] Annulation of Phthalaldehyde and 1,2-Diactivated Michael Acceptors

Fang-Gang Sun, Song Ye*
Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Fax: +86(10)62554449; e-Mail: songye@iccas.a.cn;
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Publication History

Received 17 November 2010
Publication Date:
08 March 2011 (online)

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Abstract

The diastereoselective synthesis of 2,2-disubstituted-3-hydroxy-indanones was realized by the N-heterocyclic carbene catalyzed [4+1] annulation of phthalaldehyde and 1,2-diactivated Michael acceptors, which involves a tandem process of Stetter reaction, proton shift, and aldol reaction.

Key words

[4+1] annulation - tandem reaction - N-heterocyclic carbenes - indanone - Stetter reaction

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18

At this stage, we don’t know whether the NHC leaves before or after the aldol reaction.