In Search of an Atom-Economical Synthesis of Chiral Ynamides

Jason A. Mulder; Kimberly C. M. Kurtz; Richard P. Hsung

doi:10.1055/s-2003-40817

ACCOUNT

In Search of an Atom-Economical Synthesis of Chiral Ynamides

Jason A. Mulder, Kimberly C. M. Kurtz, Richard P. Hsung*
Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
e-Mail: hsung@chem.umn.edu;

Abstract

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Abstract

Failed attempts and successes in searching for an atom-economical and efficient synthesis of chiral ynamides are described in this account. These events are illustrated in chronological order, and comparisons are made along the way to reflect other elegant methods known for preparations of ynamides and other electron deficient ynamines. The purpose of this account is to facilitate and revitalize interest in the chemistry of ynamines within the synthetic community.

1 Introduction
2 Failed Attempts in Achieving Direct Approaches
2.1 Palladium Catalyzed Cross-Coupling
2.2 Alkynyl Iodonium Salts
2.3 Base-Promoted Isomerization
3 Elimination Protocols
3.1 Lithium-Halogen Exchange
3.2 The Viehe Sequence
4 The Isomerization Protocol with Limitations
5 A Cu-Salt Catalyzed Cross-Coupling
6 Summary
7 Outlook

Key words

Ynamines - electron deficient ynamines - ynamides - base-promoted isomerization of propargyl amides - copper catalyzed cross-couplings of amides - alkynyl halides

Full Text

References

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