Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4- Conjugate Addition of β-Ketoesters to Nitroolefins

Hui      Zhang; Lin-Feng      Cun; Xiao-Mei      Zhang; Wei-Cheng      Yuan

doi:10.2174/157017810791112360

Abstract

Chiral phosphoric acid as organocatalyst for the diastereo- and enantioselectivity 1,4-conjugate addition of a variety of β-ketoesters to nitroolefins was firstly developed, providing the corresponding adducts in high yield (up to 97%) with moderate diastereoselectivities (up to 2.6:1 dr) and enantioselectivities (up to 58% ee).

Keywords: Chiral phosphoric acid, organocatalysis, asymmetric catalysis, 1,4-conjugate addition, β-ketoesters, nitroolefins

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Letters in Organic Chemistry

Title: Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4- Conjugate Addition of β-Ketoesters to Nitroolefins

Volume: 7 Issue: 3

Author(s): Hui Zhang, Lin-Feng Cun, Xiao-Mei Zhang and Wei-Cheng Yuan

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Keywords: Chiral phosphoric acid, organocatalysis, asymmetric catalysis, 1,4-conjugate addition, β-ketoesters, nitroolefins

Abstract: Chiral phosphoric acid as organocatalyst for the diastereo- and enantioselectivity 1,4-conjugate addition of a variety of β-ketoesters to nitroolefins was firstly developed, providing the corresponding adducts in high yield (up to 97%) with moderate diastereoselectivities (up to 2.6:1 dr) and enantioselectivities (up to 58% ee).

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Zhang Hui, Cun Lin-Feng, Zhang Xiao-Mei and Yuan Wei-Cheng, Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4- Conjugate Addition of β-Ketoesters to Nitroolefins, Letters in Organic Chemistry 2010; 7 (3) . https://dx.doi.org/10.2174/157017810791112360