期刊
TETRAHEDRON LETTERS
卷 56, 期 19, 页码 2377-2392出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.03.111
关键词
Terminal ynamides; Nucleophilic additions; Coupling reactions
资金
- National Institutes of Health [GM106260]
Ynamides consist of a polarized triple bond that is directly attached to a nitrogen atom carrying a sulfonyl, an alkoxycarbonyl, an acyl, or another electron withdrawing group. The triple bond polarization renders ynamides broadly useful building blocks with synthetic opportunities that go far beyond traditional alkyne chemistry. The versatile reactivity of ynamides in cycloadditions, cycloisomerizations, regioselective additions with various nucleophiles or electrophiles, ring-closing metathesis, and many other reactions has been investigated in detail during the past decades. A common feature of these methods is that the triple bond is consumed and either cleaved or transformed to a new functionality. The wealth of reports on these ynamide reactions is in stark contrast to the dearth of carbon-carbon bond formations that leave the triple bond of terminal ynamides intact. The recent introduction of effective synthetic methods for the preparation of terminal ynamides has set the stage to fully explore the synthetic potential of this intriguing class of compounds. This digest Letter summarizes the most effective routes to terminal ynamides and the current state of selective nucleophilic addition, substitution, and coupling reactions, including the first examples of asymmetric synthesis. (C) 2015 Elsevier Ltd. All rights reserved.
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