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Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization
Authors:Chong Kiat Tan  Jun Cheng ErYing-Yeung Yeung
Affiliation:Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Abstract:The asymmetric cyclization of 4,4-disubstituted 3-butenoic acids is studied. Amino-thiocarbamates are used as the catalysts and N-bromosuccinimide is used as the stoichiometric halogen source. The resulting γ-butanolide products are readily converted into the corresponding γ-butenolides (up to 58% ee) derivatives in one-pot.
Keywords:Bromolactonization   Catalysis   Lewis base   Asymmetric reaction
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