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Diastereodivergent Synthesis of 3‐Spirocyclopropyl‐2‐oxindoles through Direct Enantioselective Cyclopropanation of Oxindoles
Author(s) -
Dou Xiaowei,
Lu Yixin
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.201200655
Subject(s) - synthon , cyclopropanation , enantioselective synthesis , oxindole , catalysis , chemistry , combinatorial chemistry , stereochemistry , computer science , organic chemistry
Falling like dominos : The first direct organocatalytic asymmetric cyclopropanation reaction of oxindole was developed, in which oxindoles were employed as a dinucleophilic C 1 synthon and bromonitroolefins with a dielectrophilic center were used as a C 2 synthon (see scheme). An amino acid based multifunctional catalyst promoted the [2+1] reaction, giving the products in high yields and excellent enantioselectivities. A divergent synthesis of different stereoisomers of 3‐spirocyclopropyl‐2‐oxindoles was achieved.