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3‐(Methoxycarbonyl)Cyclobutenone as a Reactive Dienophile in Enantioselective Diels–Alder Reactions Catalyzed by Chiral Oxazaborolidinium Ions
Author(s) -
Yan Peng,
Zhong Changxu,
Zhang Jie,
Liu Yu,
Fang Huayi,
Lu Ping
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014308
Subject(s) - enantioselective synthesis , diels–alder reaction , chemistry , diene , bicyclic molecule , catalysis , octane , derivative (finance) , organic chemistry , bromide , natural rubber , financial economics , economics
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 bicyclo[4.2.0]octane derivative.