Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight
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AbstractHow can high enantioselectivity be achieved when the racemic background reaction proceeds at a rate comparable to that of the catalytic asymmetric reaction? We attempted to rationalize this counterin-tuitive observation by studying the effect of (1) catalyst structure, (2) temperature and addition sequence of components, (3) catalyst loading, and (4) Bronsted acid additives. In the course of our investigation, it was found that increasing the amount of catalyst used led to inhibition of the stoichiometric reaction. Olefinic 1,3-diol 1, 5 mol % of catalyst 3a, 1 equiv of MsOH, and NBS were added at low temperature in a specific sequence to provide the best performance for the enantioselective bromoetherification. (C) 2015 Elsevier Ltd. All rights reserved.
All Author(s) ListKe ZH, Tan CK, Liu Y, Lee KGZ, Yeung YY
Journal nameTetrahedron,Tetrahedron
Year2016
Month5
Day26
Volume Number72
Issue Number21
PublisherPERGAMON-ELSEVIER SCIENCE LTD
Pages2683 - 2689
ISSN0040-4020
LanguagesEnglish-United Kingdom
KeywordsAsymmetric halogenation; Bromoetherification; Bronsted acid; Chiral sulfide catalyst; Lewis base
Web of Science Subject CategoriesChemistry; Chemistry, Organic

Last updated on 2020-28-10 at 02:15