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
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