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An Approach to Enantioselective 5‐ endo Halo‐Lactonization Reactions
Author(s) -
Garnier Jean Marc,
Robin Sylvie,
Rousseau Gérard
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700041
Subject(s) - chemistry , enantioselective synthesis , dichloromethane , medicinal chemistry , organic chemistry , stereochemistry , catalysis , solvent
Enantioselective lactonization of 4‐substituted but‐3‐enoic acids using iodobis( N ‐methylephedrine) hexafluoroantimonate in dichloromethane at low temperatures is reported. The presence of bis( N ‐methylephedrine)silver(I) hexafluoroantimonate, derived from the excess amounts of N ‐methylephedrine and silver hexafluoroantimonate that were necessary for the generation of the iodo complex in the reaction mixture, is crucial for the success of this reaction. The different parameters of these cyclization reactions have been examined. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)