Abstract
Recent advances in the transition-metal-catalyzed enantioselective
propargylic substitution reactions of propargylic alcohol derivatives
with nucleophiles are reviewed in this article. After the disclosure
of the first example of a ruthenium-catalyzed propargylic alkylation,
various types of enantioselective propargylic substitution reactions,
including enantioselective propargylation of aromatic compounds,
have been reported in the last eight years. In addition, a variety
of enantioselective propargylic alkylations use two distinct catalysts,
where the two catalysts work cooperatively to promote the asymmetric
reactions.
1 Introduction
2 Ruthenium-Catalyzed Enantioselective Propargylic Substitution
Reactions
2.1 Propargylic Alkylation
2.2 Propargylation of Aromatic Compounds with Propargylic Alcohols
2.3 Propargylic Substitution Reactions of Propargylic Alcohols with
Alkenes
2.4 Cycloadditions between Propargylic Alcohols and 2-Naphthols
3 Copper-Catalyzed Enantioselective Propargylic Substitution
Reactions
3.1 Propargylic Amination
3.2 Ring-Opening Reactions of Ethynyl Epoxides
3.3 Propargylic Alkylation
3.4 Propargylation of Indoles
4 Cooperative Enantioselective Propargylic Alkylations Using
Transition-Metal Catalysts and Organocatalysts
4.1 With Ruthenium Catalysts
4.2 With Copper Catalysts
4.3 With Lewis Acid Catalysts
5 Cooperative Reactions Using Distinct Transition-Metal Catalysts
6 Miscellaneous Reactions
7 Conclusion
Key words
alkylation - enantioselective reaction - nucleophile - organocatalyst - propargylic alcohol - propargylic
substitution reaction
