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Synthesis 2011(12): 1984-1987  
DOI: 10.1055/s-0030-1260052
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of Bicyclo[2.2.2]octan-2-one Derivatives through an Unexpected Organocatalytic Tandem Michael-Michael Reaction

Juanjuan Yang, Huicai Huang, Zhichao Jin, Wenbin Wu, Jinxing Ye*
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
Fax: +86(21)64251830; e-Mail: yejx@ecust.edu.cn;
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Publication History

Received 11 April 2011
Publication Date:
17 May 2011 (online)

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Abstract

An organocatalytic tandem Michael-Michael reaction is developed for the simple preparation of stereo complex, polycyclic compounds from simple reactants in satisfactory yields (up to 90%) and excellent diastereoselectivities (>30:1 dr).

Key words

organocatalysis - Michael reaction - tandem reaction - α,β-unsaturated ketones

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10

The crystallographic data for structure 3h in this paper have been deposited at the Cambridge Crystallographic Data Centre, Cambridge, CB2 1EZ, United Kingdom (CCDC 804550).