Article Dans Une Revue Organic Letters Année : 2023

Enantioselective Nucleophilic Vinylic Substitution (S N V) toward 3-Alkenyl-bisoxindoles Facilitated by C6′ Steric Bulk of Cinchona Alkaloid

Résumé

A C6′ bulky substituted quinine-catalyzed S N V reaction between 3-substituted oxindole and (E)-3-(nitromethylene)-oxindole was developed. This enantioselective C(sp 3)− C(sp 2) coupling furnished bisoxindole sca olds featuring a vinylsubstituted all-carbon quaternary stereocenter with high stereoselectivities. In addition, the gram-scale synthesis and synthetic post-transformations were conducted to demonstrate the potential synthetic usefulness.

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Est décrite par hal-04260591 Image Xingyue Wang, Guishun Bai, Ruoqi Liu, Xiaoli Zhu, Xinyi Ye, et al.. Enantioselective Nucleophilic Vinylic Substitution (S N V) toward 3-Alkenyl-bisoxindoles Facilitated by C6′ Steric Bulk of Cinchona Alkaloid. France. 2023. ⟨hal-04260591⟩

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hal-04260573 , version 1 (26-10-2023)

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Xingyue Wang, Guishun Bai, Ruoqi Liu, Xiaoli Zhu, Xinyi Ye, et al.. Enantioselective Nucleophilic Vinylic Substitution (S N V) toward 3-Alkenyl-bisoxindoles Facilitated by C6′ Steric Bulk of Cinchona Alkaloid. Organic Letters, 2023, 25 (32), pp.5941-5945. ⟨10.1021/acs.orglett.3c01964⟩. ⟨hal-04260573⟩
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