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Highly Enantioselective Synthesis of Chiral Pyranonaphthoquinone‐Fused Spirooxindoles through Organocatalytic Three‐Component Cascade Reactions
Author(s) -
Zhao HongWu,
Li Bo,
Tian Ting,
Meng Wei,
Yang Zhao,
Song XiuQing,
Chen XiaoQin,
Pang HaiLiang
Publication year - 2015
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.201500152
Subject(s) - chemistry , malononitrile , thiourea , enantioselective synthesis , yield (engineering) , cinchona , organocatalysis , cascade reaction , combinatorial chemistry , component (thermodynamics) , cascade , organic chemistry , catalysis , chromatography , materials science , physics , metallurgy , thermodynamics
In the presence of cinchona‐thiourea organocatalyst C1 , the developed organocatalytic three‐component cascade reaction of isatins, malononitrile, and 2‐hydroxynaphthalene‐1,4‐diones readily proceeded to furnish chiral pyranonaphthoquinone‐fused spirooxindoles in excellent chemical yields and high enantioselectivities (up to 99 % yield and 97 % ee ). The absolute configurations of the spirooxindoles were assigned on the basis of an X‐ray single crystal structure. Moreover, a reaction mechanism is proposed that accounts for the stereocontrolled formation of the chiral spirooxindoles,.