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Palladium‐Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2‐Arylidene‐1,3‐Indandiones: Synthesis of Tetrahydrofuran‐Fused Spirocyclic 1,3‐Indandiones
Author(s) -
Zhang Huihui,
Gao Xing,
Jiang Feng,
Shi Wangyu,
Wang Wei,
Wu Yongjun,
Zhang Cheng,
Shi Xueyan,
Guo Hongchao
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000762
Subject(s) - chemistry , cycloaddition , tetrahydrofuran , yield (engineering) , phosphoramidite , palladium , catalysis , ligand (biochemistry) , medicinal chemistry , organic chemistry , receptor , dna , biochemistry , materials science , oligonucleotide , solvent , metallurgy
An asymmetric [3+2] cycloaddition of 2‐arylidene‐1,3‐indandiones with vinylethylene carbonates (VECs) had been achieved in the presence of Pd 2 dba 3 · CHCl 3 and axially chiral phosphoramidite ligand. The reaction of various substituted VECs and 2‐arylidene‐1,3‐indandiones proceeded smoothly under mild conditions, giving the highly functionalized spirocyclic 1,3‐indanedione derivatives in good to excellent yield with moderate diastereoselectivity and high enantioselectivity. The reaction on the gram scale had also been demonstrated.