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Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides
- Authors
- Koo, Jaeyoung; Park, Hyun-Sub; Shin, Seunghoon
- Issue Date
- Feb-2013
- Publisher
- Elsevier BV
- Keywords
- 1,6-Enyne; Cycloisomerization; Silver catalysis; Propiolamide; Silver carbenoid; Gold catalysis
- Citation
- Tetrahedron Letters, v.54, no.8, pp 834 - 839
- Pages
- 6
- Indexed
- SCI
SCIE
SCOPUS
- Journal Title
- Tetrahedron Letters
- Volume
- 54
- Number
- 8
- Start Page
- 834
- End Page
- 839
- ISSN
- 0040-4039
- Abstract
- Silver-catalyzed cycloisomerizations of 1,6-enynes derived from propiolamides led to a selective formation of Alder-ene type 1,4-dienes. Interestingly, AgNTf2 outperformed gold or platinum catalysts in terms of selectivity and reactivity, providing the 1,4-dienes at room temperature. The presence of C(5) carbonyl group in combination with Ag salts is key to the selectivity and the beta-oxo coordinated silver carbenoids were proposed as an intermediate based on the reaction profiles.
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Related Researcher
- Shin, Seung hoon
- COLLEGE OF NATURAL SCIENCES (DEPARTMENT OF CHEMISTRY)