4.4 Article

Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline

Journal

TETRAHEDRON
Volume 66, Issue 21, Pages 3801-3813

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.047

Keywords

Lewis-base catalysis; N-heterocyclic carbene; Organocatalysis; Carboxyl transfer; Spiro[pyrrolidine-3,3 '-oxindole]

Funding

  1. Royal Society
  2. EPSRC
  3. AstraZeneca

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NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

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