Diastereodivergent synthesis of 3-spirocyclopropyl-2-oxindoles through direct enantioselective cyclopropanation of oxindoles
Dou, X. Lu, Y.
Dou, X.
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Abstract
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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Keywords
asymmetric synthesis, cyclopropanation, domino reactions, organocatalysis, oxindole
Source Title
Chemistry - A European Journal
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Date
2012-07-02
DOI
10.1002/chem.201200655
Type
Article