Chapter 3. Addition of Terminal Acetylides to C[DOUBLE BOND]O and C[DOUBLE BOND]N Electrophiles

  1. Prof. Dr. François Diederich3,
  2. Prof. Dr. Peter J. Stang4 and
  3. Prof. Dr. Rik R. Tykwinski5
  1. Patrick Aschwanden1 and
  2. Erick M. Carreira2

Published Online: 24 OCT 2005

DOI: 10.1002/3527605487.ch3

Acetylene Chemistry: Chemistry, Biology, and Material Science

Acetylene Chemistry: Chemistry, Biology, and Material Science

How to Cite

Aschwanden, P. and Carreira, E. M. (2004) Addition of Terminal Acetylides to C[DOUBLE BOND]O and C[DOUBLE BOND]N Electrophiles, in Acetylene Chemistry: Chemistry, Biology, and Material Science (eds F. Diederich, P. J. Stang and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527605487.ch3

Editor Information

  1. 3

    Laboratorium für Organische Chemie, ETH Hönggerberg, HCI, CH-8093 Zürich, Switzerland

  2. 4

    Department of Chemistry, University of Utah, 315S 1400E, Rm. 2020, 84112 Salt Lake City, USA

  3. 5

    Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Author Information

  1. 1

    Laboratorium für Organische Chemie, ETH Zürich, 8093 Zürich, Switzerland

  2. 2

    Laboratory of Organic Chemistry, ETH Hoenggerberg, HCI, 8093 Zürich, Switzerland

Publication History

  1. Published Online: 24 OCT 2005
  2. Published Print: 14 DEC 2004

ISBN Information

Print ISBN: 9783527307814

Online ISBN: 9783527605484

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Keywords:

  • acetylene chemistry;
  • biology and material science;
  • addition of terminal acetylides;
  • C[DOUBLE BOND]O and C[DOUBLE BOND]N electrophiles;
  • additions with metal acetylides;
  • nucleophilic C[DOUBLE BOND]O additions;
  • experimental procedures

Summary

This chapter contains sections titled:

  • Introduction

  • Background

  • Additions with Stoichiometric Amounts of Metal Acetylides

  • Nucleophilic C[DOUBLE BOND]O Additions involving the Use of Zn(II) Salts

  • Acetylene Additions to C[DOUBLE BOND]N Electrophiles

  • Conclusion

  • Experimental Procedures

    • General Procedure for the Enantioselective Alkynylation of Aldehydes by the Use of Stoichiometric Amounts of Zn(OTf)2

    • General Procedure for the Zn(OTf)2-Catalyzed Enantioselective Alkynylation of Aldehydes

    • General Procedure for the Enantioselective Alkynylation of Ketones Catalyzed by Zn(salen) Complexes

    • General Procedure for the Zn(OTf)2-Catalyzed Diastereoselective Alkynylation of N-Glycosyl Nitrones

    • General Procedure for the Et2Zn-Catalyzed Diastereoselective Alkynylation of Chiral Nitrones

    • General Procedure for the CuBr-Catalyzed Enantioselective Preparation of Propargylamines

    • General Procedure for the [IrCl(COD)]2-Catalyzed Alkynylation of Imines