Journal
ORGANIC LETTERS
Volume 19, Issue 2, Pages 344-347Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03520
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Funding
- Creative Research Initiative Grant [2014R1A3A2030423]
- Bio AMP
- Medical Technology Development Program through the National Research Foundation of Korea (NRF) - Korean Government (Ministry of Science, ICT AMP
- Future Planning) [2012M3A9C4048780]
- BK21 Plus Program
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Pyrimidodiazepine derivatives underwent an unexpected gold-catalyzed retro-Mannich-type carbon-carbon bond cleavage and intramolecular nucleophilic cyclization. The pyrimidodiazepines bearing an alkyne moiety showed novel orthogonal reactivity in the presence of a gold catalyst, as opposed to the alkynophilicity that is commonly observed with gold catalysts. The ring transformation reaction of pyrimidodiazepines probably proceeds through an acyclic iminium intermediate. The potential of this synthetic method for the skeletal diversification of pyrimidine-containing macrocycles was also demonstrated.
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