4.5 Article

Enantioselective Synthesis of Spiro[indoline-3,2′-pyrroles] through N-Heterocyclic-Carbene-Catalyzed Formal [3+2] Annulation

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 34, Pages 5653-5658

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600958

Keywords

Carbenes; Organocatalysis; Nitrogen heterocycles; Spiro compounds; Annulation

Funding

  1. National Natural Science Foundation [21172099, 21372106]
  2. Program 111

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An N-heterocyclic-carbene-catalyzed asymmetric formal [3+2] annulation reaction of isatin N-Boc ketimines (Boc = tert-butyloxycarbonyl) and 3-bromoenals was developed for the construction of spiro[indoline-3,2'-pyrrole] derivatives with one quaternary chiral center in good yields (up to 81 % yield) with excellent enantioselectivity (up to 99 % ee).

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