Synthesis and cardiotropic activity of stereoisomeric 1-[2-(3,4-dimethoxyphenyl) ethyl]-2-methyl-4-ethynyl-4-acyloxy-trans-decahydroquinolines

The first enantioselective sequential phosphine-catalyzed (SPC as abbreviation) mode for the formation of tetrahydroquinolines with an ethynyl-substituted all-carbon quaternary stereogenic center is reported. In this SPC process, a novel [4 + 2] annulation process was devised employing α-substituted allenoates as C2 synthons (α–β′, 1,2-dipole) for the first time. 3-Ethynyl-substituted tetrahydroquinolines were readily prepared in good yields and high enantioselectivities.

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Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3-Ethynyl-Substituted Tetrahydroquinolines

Zhang

Jin

Feng

et al. 2019

Org. Lett.

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Synthesis and cardiotropic activity of stereoisomeric 1-[2-(3,4-dimethoxyphenyl) ethyl]-2-methyl-4-ethynyl-4-acyloxy-trans-decahydroquinolines

Abstract: The carbinols (I) are coupled with the carboxylic chlorides (II) or (IV) to give the esters (III).

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Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3-Ethynyl-Substituted Tetrahydroquinolines

Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3-Ethynyl-Substituted Tetrahydroquinolines

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