6533b7d0fe1ef96bd125b4a1

RESEARCH PRODUCT

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

Carlos Vila DescalsNisshanth Raj DharmarajAntonio FaubelGonzalo Blay LlinaresMaría Luz Cardona PrósperM. Carmen MuñozJosé Ramón Pedro

subject

CatàlisiQuímica orgànica

description

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.

yearjournalcountryeditionlanguage
2019-01-01
10.1002/ejoc.201900328https://hdl.handle.net/10550/73776