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Highly Stereoselective Radical Cyclization of Haloacetals Controlled by the Acetal Center
Author(s) -
Villar Félix,
KollyKovac Tanja,
Equey Olivier,
Renaud Philippe
Publication year - 2003
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.200390180
Subject(s) - stereocenter , acetal , stereoselectivity , chemistry , stereochemistry , radical cyclization , center (category theory) , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , crystallography
A systematic investigation of radical haloacetal cyclizations (Ueno–Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and γ ‐lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)‐eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.