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Cyclobutenone has been used as a highly reactive dienophile in Diels-Alder reactions, however, no enantioselective example has been reported. We disclose herein a chiral oxazaborolidine-aluminum bromide catalyzed enantioselective Diels-Alder reaction of 3-alkoxycarbonyl cyclobutenone with a variety of dienes. Furthermore, a total synthesis of (-)-kingianin F was completed for the first time via enantioenriched cycloadduct bicyclo4.2.0octane derivative.
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Peng Yan
Changxu Zhong
Jie Zhang
Angewandte Chemie International Edition
Fudan University
Nankai University
Changchun University of Technology
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Yan et al. (Tue,) studied this question.
synapsesocial.com/papers/69d964322a25b240b7a3c103 — DOI: https://doi.org/10.1002/anie.202014308