TY - JOUR
T1 - Diversity-Oriented Synthesis of Spirocyclohexene Indane-1,3-diones and Coumarin-Fused Cyclopentanes via an Organobase-Controlled Cascade Reaction
AU - Wang, Min
AU - Tseng, Ping Yao
AU - Chi, Woei Jye
AU - Suresh, Sundaram
AU - Edukondalu, Athukuri
AU - Chen, Yi Ru
AU - Lin, Wenwei
N1 - Funding Information:
The authors thank the Ministry of Science and Technology of the Republic of China (MOST 107‐2628‐M‐003‐001‐MY3) for financial support.
Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020
Y1 - 2020
N2 - An organobase-controlled, divergent cascade reaction to construct spirocyclohexene indane-1,3-diones and coumarin-fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6-addition of 3-homoacylcoumarins to the indanedione-derived acceptors and further regio/chemoselective reaction that preferentially resulted in spiro systems and fused cyclopentanes in a diversity-oriented manner. The 1,6-addition/aldol and 1,6-addition/vinylogous Michael addition cascade processes were controlled by different base/solvent systems to the predominant formation of one of the two carbocyclic compounds. (Figure presented.).
AB - An organobase-controlled, divergent cascade reaction to construct spirocyclohexene indane-1,3-diones and coumarin-fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6-addition of 3-homoacylcoumarins to the indanedione-derived acceptors and further regio/chemoselective reaction that preferentially resulted in spiro systems and fused cyclopentanes in a diversity-oriented manner. The 1,6-addition/aldol and 1,6-addition/vinylogous Michael addition cascade processes were controlled by different base/solvent systems to the predominant formation of one of the two carbocyclic compounds. (Figure presented.).
KW - 1,6-addition
KW - aldol reaction
KW - Diversity-oriented synthesis
KW - spiro and fused systems
KW - vinylogous Michael addition
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U2 - 10.1002/adsc.202000597
DO - 10.1002/adsc.202000597
M3 - Article
AN - SCOPUS:85087814746
VL - 362
SP - 3407
EP - 3415
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 16
ER -