Synlett 2014; 25(12): 1685-1691
DOI: 10.1055/s-0033-1339124
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© Georg Thieme Verlag Stuttgart · New York

Highly Enantioselective Asymmetric Michael Addition Reactions with New Chiral Multisite Phase-Transfer Catalysts

Sivamani Jayaraman
Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India   Fax: +91(452)2459181   eMail: drasiva@gmail.com
,
Duraimurugan Kumaraguru
Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India   Fax: +91(452)2459181   eMail: drasiva@gmail.com
,
Jesin Beneto Arockiam
Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India   Fax: +91(452)2459181   eMail: drasiva@gmail.com
,
Subha Paulpandian
Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India   Fax: +91(452)2459181   eMail: drasiva@gmail.com
,
Balasaravanan Rajendiran
Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India   Fax: +91(452)2459181   eMail: drasiva@gmail.com
,
Ayyanar Siva*
Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India   Fax: +91(452)2459181   eMail: drasiva@gmail.com
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Publikationsverlauf

Received: 13. März 2014

Accepted after revision: 22. April 2014

Publikationsdatum:
12. Juni 2014 (online)


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Abstract

Highly enantioselective Michael addition reactions of diethyl malonate to various chalcones have been achieved under mild chiral multisite phase-transfer reaction conditions by the successful utilization of 2,4,6-(triscinchoniummethyl)phenyl-1,3,5-triazines as new chiral quaternary ammonium catalysts. This simple asymmetric Michael addition process was found to be quite effective and to obtain Michael adducts with very good yields and enantiomeric excesses.

Supporting Information