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Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF 3 S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones
Author(s) -
Eitzinger Andreas,
Otevrel Jan,
Haider Victoria,
Macchia Antonio,
Massa Antonio,
Faust Kirill,
Spingler Bernhard,
Berkessel Albrecht,
Waser Mario
Publication year - 2021
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.202100029
Subject(s) - chemistry , bifunctional , enantioselective synthesis , salt (chemistry) , heteroatom , catalysis , ammonium , derivative (finance) , organocatalysis , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , ring (chemistry) , financial economics , economics
We herein report the ammonium salt‐catalyzed synthesis of chiral 3,3‐disubstituted isoindolinones bearing a heteroatom functionality in the 3‐position. A broad variety of differently substituted CF 3 S‐ and RS‐derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof‐of‐concept for the racemic synthesis of the analogous F‐containing products was obtained as well, giving access to one of the rare examples of a fairly stable α‐F‐α‐amino acid derivative.