Divergent Cyclization Reactions of Morita-Baylis-Hillman Carbonates of 2-Cyclohexenone and Isatylidene Malononitriles.
Zwitterionic dienolates generated from Morita-Baylis-Hillman carbonates of cyclohexen-2-one and a phenolic tertiary amine catalyst underwent divergent cyclization reactions with isatylidene malononitriles. A new [4 + 2] stepwise cyclization process was disclosed to deliver complex bridged spirooxindoles after the initial δ'-regioselective Rauhut-Currier-type reaction with N-methyl electrophiles by the catalysis of β-isocupreidine, while spirooxindoles incorporating an aromatic chromene motif were generated with N-MOM acceptors in the presence of α-isocupreine through different domino transformations.
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
Jing
J
Peng
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
Guang-Yao
GY
Ran
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
Wei
W
Du
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.|College of Pharmacy, Third Military Medical University , Shapingba, Chongqing 400038, China.
Ying-Chun
YC
Chen