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Scaffold‐Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin‐3,2′‐oxindoles] with Structural Diversity through Catalytic Isatin‐Derived 1,3‐Dipolar Cycloadditions
Author(s) -
Shi Feng,
Tao ZhongLin,
Luo ShiWei,
Tu ShuJiang,
Gong LiuZhu
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.201200358
Subject(s) - isatin , stereocenter , oxindole , enantioselective synthesis , catalysis , chemistry , cycloaddition , 1,3 dipolar cycloaddition , stereochemistry , combinatorial chemistry , organic chemistry
Catalytic asymmetric construction of the biologically important spiro[pyrrolidin‐3,2′‐oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee ) has been established by using an organocatalytic 1,3‐dipolar cycloaddition of isatin‐based azomethine ylides. This protocol represents the first example of catalytic asymmetric 1,3‐dipolar cycloadditions involving azomethine ylides generated in situ from unsymmetrical cyclic ketones. In addition, theoretical calculations were performed on the transition state of the reaction to understand the stereochemistry. Preliminary bioassays with these spiro[pyrrolidin‐3,2′‐oxindole] revealed that several compounds showed moderate cytotoxicity to SW116 cells.