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Enantioselective Synthesis of Spirothiazolones via Cooperative Catalysis
Author(s) -
Franc Michael,
Císařová Ivana,
Veselý Jan
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.202100571
Subject(s) - enantioselective synthesis , chemistry , cyclopentane , catalysis , thiazole , combinatorial chemistry , palladium , chirality (physics) , organocatalysis , stereochemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Cooperative amino‐ and palladium catalysis utilizing heterocyclic systems containing strongly coordinating and adsorptive sulfur atom remains an underdeveloped area. Herein, we describe an enantioselective cyclization of enals with thiazole derivatives catalyzed with the combination of achiral Pd(0) complexes and chiral secondary amines. Chiral spirocyclic thiazolones were produced in yields ranging from 41% to 98% with stereoselectivities (from 5:1 to 12:1 dr, and 95–99% ee). Moreover, the developed strategy allows access to highly substituted chiral cyclopentane derivatives by additional transformations of spirocyclic thiazolones.