Regio‐, Diastereo‐, and Enantioselective Organocatalytic Addition of 4‐Substituted Pyrazolones to Isatin‐Derived Nitroalkenes
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Regio‐, Diastereo‐, and Enantioselective Organocatalytic Addition of 4‐Substituted Pyrazolones to Isatin‐Derived Nitroalkenes

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Regio‐, Diastereo‐, and Enantioselective Organocatalytic Addition of 4‐Substituted Pyrazolones to Isatin‐Derived Nitroalkenes

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Vila Descals, Carlos; Dharmaraj, Nisshanth Raj; Faubel, Antonio; Blay Llinares, Gonzalo Perfil; Cardona Prósper, María Luz; Muñoz, M. Carmen; Pedro, José Ramón
This document is a artículoDate2019
Hydroquinine 2,5‐diphenyl‐4,6‐pyrimidinediyl diether [(DHQ)2Pyr] catalyzed the regio‐, diastereo‐, and enantioselective addition of 4‐substituted pyrazolones to isatin‐derived nitroalkenes, providing a variety of chiral alkenylpyrazolone adducts containing a tetrasubstituted stereocenter bearing an oxindole moiety with excellent yields, regioselectivity, and diastereoselectivity, as well as a moderate enantioselectivity (up to 98 % yield, > 20:1 E/Z ratio dr and 78 % ee). The reaction harnesses a nitroalkene as an alkenylating agent through a Nucleophilic Vinylic Substitution (SNV) reaction.

    Vila Descals, Carlos Dharmaraj, Nisshanth Raj Faubel, Antonio Blay Llinares, Gonzalo Cardona Prósper, María Luz Muñoz, M. Carmen Pedro, José Ramón 2019 Regio‐, Diastereo‐, and Enantioselective Organocatalytic Addition of 4‐Substituted Pyrazolones to Isatin‐Derived Nitroalkenes European Journal of Organic Chemistry 2019 19 3040 3044
https://doi.org/10.1002/ejoc.201900328

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