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Enantioselective Zinc/BINOL-Catalysed Alkynylation of Aldimines Generated in Situ from α-Amido Sulfones

  1. Dr. Gonzalo Blay,
  2. Ana Brines,
  3. Alicia Monleón,
  4. Prof. Dr. José R. Pedro*

Article first published online: 19 JAN 2012

DOI: 10.1002/chem.201102909

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 8, pages 2440–2444, February 20, 2012

Additional Information

How to Cite

Blay, G., Brines, A., Monleón, A. and Pedro, J. R. (2012), Enantioselective Zinc/BINOL-Catalysed Alkynylation of Aldimines Generated in Situ from α-Amido Sulfones. Chem. Eur. J., 18: 2440–2444. doi: 10.1002/chem.201102909

Author Information

  1. Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (Spain), Fax: (+34) 963544328

*Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (Spain), Fax: (+34) 963544328

Publication History

  1. Issue published online: 10 FEB 2012
  2. Article first published online: 19 JAN 2012
  3. Manuscript Received: 16 SEP 2011

Funded by

  • Ministerio de Ciencia e Innovación
  • FEDER. Grant Number: CTQ2009–13083
  • Generalitat Valenciana. Grant Number: ACOMP/2011/267

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Keywords:

  • alkynylation;
  • asymmetric catalysis;
  • enantioselectivity;
  • nucleophilic addition;
  • propargylic amines

Abstract

Chiral nonracemic N-Cbz-protected propargylic amines have been prepared by the addition of terminal alkynes to imines generated in situ from α-amido sulfones in the presence of diethylzinc and BINOL-type ligands as catalysts. The reactions give good yields and high enantioselectivities (ee values up to 95 %) for a good number of aromatic and heteroaromatic α-amido sulfones and alkynes.

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