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Synthesis 2007(11): 1729-1732  
DOI: 10.1055/s-2007-965966
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© Georg Thieme Verlag Stuttgart · New York

Synthesis and Use of 3,3′-Bimorpholine Derivatives in Asymmetric Michael Addition and Intramolecular Aldol Reaction

Sarah Sulzer-Mosséa, Marju Laarsb, Kadri Kriisb, Tõnis Kanger*b, Alexandre Alexakis*a
a Department of Organic Chemistry, University of Geneva, Sciences II, 30, quai Ernest Ansermet, 1211 Geneva 4, Switzerland
Fax: +41(22)3793215; e-Mail: alexandre.alexakis@chiorg.unige.ch;
b Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia
Fax: +3726202828; e-Mail: kanger@chemnet.ee;
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Publication History

Received 2 February 2007
Publication Date:
28 February 2007 (online)

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Abstract

The synthesis of 3,3′-bimorpholine and its N-alkyl derivatives is described. These new diamine derivatives were revealed to be efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroalkenes with excellent enantioselectivity (up to 90% ee). The potential of these organocatalysts was also demonstrated for the highly enantioselective intramolecular aldol reaction affording the Wieland-Miescher ketone with tremendous enantioselectivity (up to 95% ee).

Key words

diamine - asymmetric catalysis - organocatalysis - aldol reaction - Michael addition