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A Highly Enantioselective One‐Pot Synthesis of Spirolactones by an Organocatalyzed Michael Addition/Cyclization Sequence
Author(s) -
Sternativo Silvia,
Calandriello Antonella,
Costantino Ferdinando,
Testaferri Lorenzo,
Tiecco Marcello,
Marini Francesca
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201104819
Subject(s) - michael reaction , enantioselective synthesis , sequence (biology) , electrophile , chemistry , combinatorial chemistry , computer science , organic chemistry , catalysis , biochemistry
Spiroring in control : A novel organocatalytic Michael addition/cyclization sequence based on the bis(electrophilic) properties of vinyl selenones has been successfully employed for the synthesis of densely functionalized spirocyclic compounds (see scheme). By using a simple one‐pot procedure and mild reaction conditions, spirocyclic compounds were synthesized in high yields and with high levels of enantioselectivity (90–98 % ee ).