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Enantioselective Radical Cyclizations: A New Approach to Stereocontrol of Cascade Reactions
Author(s) -
Miyabe Hideto,
Takemoto Yoshiji
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700864
Subject(s) - stereocenter , chemistry , enantioselective synthesis , moiety , quaternary carbon , intramolecular force , cascade reaction , lewis acids and bases , cascade , chiral lewis acid , radical cyclization , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , chromatography
Stereocontrol in a cascade radical addition–cyclization–trapping reaction was achieved by a new approach, which utilizes a hydroxamate ester moiety as a coordinating chiral Lewis acid tether between two radical acceptors. A remarkable feature of this reaction is the construction of three bonds and tertiary and quaternary stereogenic centers through both inter‐ and intramolecular carbon–carbon bond‐forming processes. The chiral Lewis acid mediated reaction of oxime ethers also proceeded smoothly with good enantio‐ and diastereoselectivities, indicating the usefulness of the cascade approach for the asymmetric synthesis of various γ‐lactams.