Asymmetric Michael/Aromatization Reaction of Azlactones to α,β‐Unsaturated Pyrazolones with C‐4 Regioselectivity Catalyzed by an Isosteviol‐Derived Thiourea Organocatalyst | Zendy

Geng ZhiCong | Zendy; Chen Xiang | Zendy; Zhang JinXin | Zendy; Li Ning | Zendy; Chen Jian | Zendy; Huang XiaoFei | Zendy; Zhang ShaoYun | Zendy; Tao JingChao | Zendy; Wang XingWang | Zendy

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Asymmetric Michael/Aromatization Reaction of Azlactones to α,β‐Unsaturated Pyrazolones with C‐4 Regioselectivity Catalyzed by an Isosteviol‐Derived Thiourea Organocatalyst

Author(s) -

Geng ZhiCong,

Chen Xiang,

Zhang JinXin,

Li Ning,

Chen Jian,

Huang XiaoFei,

Zhang ShaoYun,

Tao JingChao,

Wang XingWang

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201300524

Subject(s) - pyrazolones , chemistry , thiourea , aromatization , organocatalysis , organic chemistry , michael reaction , regioselectivity , catalysis , amine gas treating , enantioselective synthesis

Pyrazoles are an important class of molecular structures with significant biological and pharmaceutical activities. Herein, heterocyclic compounds containing both a pyrazole motif and a masked amino acid structure are synthesized through the asymmetric Michael/aromatization of azlactones to α,β‐unsaturated pyrazolones by using isosteviol‐derived amine thiourea as the organocatalyst. The products are obtained in good yields (up to 93 %) with good diastereoselectivities and good enantioselectivities (up to >10:1 dr , 97 % ee ).

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