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Catalytic Enantioselective Dieckmann‐Type Annulation: Synthesis of Pyrrolidines with Quaternary Stereogenic Centers
Author(s) -
Hargrave Jonathan D.,
Allen Joseph C.,
KociokKöhn Gabriele,
Bish Gerwyn,
Frost Christopher G.
Publication year - 2010
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.200907067
Subject(s) - stereocenter , enantioselective synthesis , annulation , stereochemistry , type (biology) , chemistry , ligand (biochemistry) , substrate (aquarium) , combinatorial chemistry , computer science , catalysis , organic chemistry , biology , receptor , ecology , biochemistry
A new trick for an old dog : A Dieckmann‐type cyclization was used to synthesize the title compounds with up to 96 % ee (see scheme; Bn=benzyl). The presence of a β coordinating functionality in the substrate induces a competition between cyclization and elimination pathways that is influenced by the nature of the chiral ligand. A mechanistic rationale is proposed to account for these observations.