0000000000130954
AUTHOR
Antonio Faubel
Regio‐, Diastereo‐, and Enantioselective Organocatalytic Addition of 4‐Substituted Pyrazolones to Isatin‐Derived Nitroalkenes
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.
Regio-, Diastereo-, and Enantioselective Organocatalytic Addition of 4-Substituted Pyrazolones to Isatin-Derived Nitroalkenes
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CCDC 1899761: Experimental Crystal Structure Determination
Related Article: Carlos Vila, Nisshanth Raj Dharmaraj, Antonio Faubel, Gonzalo Blay, M. Luz Cardona, M. Carmen Muñoz, Jose R. Pedro|2019|Eur.J.Org.Chem.|2019|3040|doi:10.1002/ejoc.201900328