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Core Structure‐Based Design of Organocatalytic [3+2]‐Cycloaddition Reactions: Highly Efficient and Stereocontrolled Syntheses of 3,3′‐Pyrrolidonyl Spirooxindoles
Author(s) -
Tan Bin,
Zeng Xiaofei,
Leong Wendy Wen Yi,
Shi Zugui,
Barbas Carlos F.,
Zhong Guofu
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103449
Subject(s) - cycloaddition , oxindole , computer science , enantioselective synthesis , imide , organocatalysis , combinatorial chemistry , core (optical fiber) , chemistry , stereochemistry , organic chemistry , catalysis , telecommunications
Extraordinary levels of stereocontrol were achieved in an efficient organocatalytic asymmetric [3+2]‐cycloaddition reaction between an α‐isothiocyanato imide and various methyleneindolinones. Simple precursors were used for the rapid construction of spirocyclic oxindole derivatives with high enantiopurity and structural diversity, thus providing a new avenue of significance to medicinal chemistry and diversity‐oriented synthesis.