Enantioselective Organocatalytic Michael Addition of Cyclopentane-1,2-diones to Nitroolefins

Gert Preegel; Artur Noole; Kaja Ilmarinen; Ivar Järving; Tõnis Kanger; Tõnis Pehk; Margus Lopp

doi:10.1055/s-0034-1378374

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(19): 2595-2600
DOI: 10.1055/s-0034-1378374

paper

Enantioselective Organocatalytic Michael Addition of Cyclopentane-1,2-diones to Nitroolefins

Autor*innen

Gert Preegel

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Artur Noole

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Kaja Ilmarinen

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Ivar Järving

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Tõnis Kanger

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Tõnis Pehk

^bNational Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia Fax: +372(620)2808 eMail: margus.lopp@ttu.ee
Margus Lopp*

^aDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

Abstract

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Abstract

Organocatalytic Michael additions of cyclopentane-1,2-dione to different nitroolefins have been investigated. Cyclopentane-1,2-dione undergoes an organocatalytic reaction with substituted nitroolefins giving 3-substituted products in good to high yields (48–97%) and good stereoselectivity (up to 76% ee).

Key words

Michael addition - asymmetric synthesis - asymmetric catalysis - enantioselectivity - electrophilic addition - ketones

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Referenzen

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