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Synthesis of Enantioenriched 3‐Amino‐3‐Substituted Oxindoles by Stereoselective Mannich Reaction Catalyzed by Supported Bifunctional Thioureas.
Author(s) -
RodríguezFerrer Patricia,
SanzNovo Miguel,
Maestro Alicia,
Andrés José M.,
Pedrosa Rafael
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900414
Subject(s) - chemistry , bifunctional , nucleophile , isatin , diastereomer , mannich reaction , catalysis , stereoselectivity , organic chemistry , organocatalysis , enantioselective synthesis , derivative (finance) , nucleophilic addition , combinatorial chemistry , financial economics , economics
Enantioenriched 3‐amino‐3‐substituted oxindoles have been obtained by addition of different nucleophiles to N ‐Boc ketimines derived from isatin catalyzed by chiral bifunctional supported thioureas. The Mannich reaction occurs with excellent enantioselection, but poor diastereoselection when prochiral nucleophiles were used. The supported catalyst were recovered and reused for five times without loss of activity. The mixture of diastereoisomers formed when a prochiral structure was used as nucleophile was converted into a single enantioenriched pyrazolyl derivative.