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Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans
Author(s) -
Belmessieri Dorine,
de la Houpliere Alix,
Calder Ewen D. D.,
Taylor James E.,
Smith Andrew D.
Publication year - 2014
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.201402684
Subject(s) - michael reaction , diastereomer , intramolecular force , chemistry , cinchona , enone , enantioselective synthesis , tetrahydrofuran , stereochemistry , catalysis , organic chemistry , solvent
Abstract A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available ( S )‐(−)‐tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r. syn / anti , 99 % ee syn ), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti ‐diastereoisomers as the major product (up to 10:90 d.r. syn / anti , 99 % ee anti ).