2014Organic LettersOpen access

Highly Enantioselective Organocatalyzed Vinylogous Michael-Type Reaction for the Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters

Qiao Chen, Guoqiang Wang, Xianxing Jiang, Zhaoqing Xu, Li Lin, Rui Wang

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Abstract

The first example of a highly enantioselective vinylogous Michael-type reaction of β,β-disubstituted nitroalkenes is disclosed. A series of biologically important chiral oxindoles, featuring a trifluoromethylated all-carbon quaternary chiral center, were obtained in good yields with excellent enantioselectivities (up to >99% ee).

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What this paper is about

The first example of a highly enantioselective vinylogous Michael-type reaction of β,β-disubstituted nitroalkenes is disclosed. A series of biologically important chiral oxindoles, featuring a trifluoromethylated all-carbon quaternary chiral center, were obtained in good yields with excellent enantioselectivities (up to >99% ee).

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Available abstract

The first example of a highly enantioselective vinylogous Michael-type reaction of β,β-disubstituted nitroalkenes is disclosed. A series of biologically important chiral oxindoles, featuring a trifluoromethylated all-carbon quaternary chiral center, were obtained in good yields with excellent enantioselectivities (up to >99% ee).

Key concepts: Stereocenter, Enantioselective synthesis, Chemistry, Quaternary carbon, Organocatalysis, Asymmetric carbon, Organic chemistry, Carbon fibers

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