Matches in SemOpenAlex for { <https://semopenalex.org/work/W223649340> ?p ?o ?g. }
Showing items 1 to 63 of
63
with 100 items per page.
- W223649340 abstract "Author(s): Pierce, Conor John | Advisor(s): Larsen, Catharine H. | Abstract: The Larsen group specializes in maximizing the potential of simple organic substrates through single-step, multicomponent reactions to yield complex compounds with potential therapeutic and synthetic applications. Combining a carbonyl, an amine, and a terminal alkyne under a variety of novel conditions provides a range of propargylamines. Attempts towards the incorporation of labile protecting groups on propargylamines led to the discovery of the first catalytic three-component method able to incorporate electron-poor amines, specifically p-toluenesulfonamide. Mechanistic studies showed copper(II) triflate to be unique in its ability to catalyze both the condensation of p-toluenesulfonamide onto an aldehyde and sequential coupling with a terminal alkyne. This method also provided a rare example of a three-component coupling between cyclohexanone, benzylamine, and 1-octyne. Investigations into the synthesis of this cyclohexanone-derived propargylamine led to an efficient copper(II) chloride catalyzed reaction yielding fully-substituted centers on cyclohexane rings. Equimolar amounts of starting reagents, low-catalyst loading, and water as the sole by-product of this reaction leant to its efficacy. Inclusion of Lewis acidic titanium tetraethoxide provided a Cu/Ti catalyzed method of novel scope, allowing for the first coupling of acyclic ketones with amines and alkynes to give fully-substituted amine-bearing carbon centers in a single step. An alternate route to these densely-functionalized substrates was discovered to be a unique tandem hydroamination/alkynylation reaction. Markovnikov addition of an amine across a terminal alkyne yields enamine which, upon tautamerization to ketimine, is coupled with a second equivalent of the same alkyne to form propargylamine." @default.
- W223649340 created "2016-06-24" @default.
- W223649340 creator A5038989029 @default.
- W223649340 date "2013-01-01" @default.
- W223649340 modified "2023-09-27" @default.
- W223649340 title "Multi-Component Copper Catalyzed Methods to Access Highly-Substituted Amine-Bearing Carbon Centers from Simple Starting Materials" @default.
- W223649340 hasPublicationYear "2013" @default.
- W223649340 type Work @default.
- W223649340 sameAs 223649340 @default.
- W223649340 citedByCount "0" @default.
- W223649340 crossrefType "journal-article" @default.
- W223649340 hasAuthorship W223649340A5038989029 @default.
- W223649340 hasConcept C131779359 @default.
- W223649340 hasConcept C161790260 @default.
- W223649340 hasConcept C178790620 @default.
- W223649340 hasConcept C185592680 @default.
- W223649340 hasConcept C21774173 @default.
- W223649340 hasConcept C21951064 @default.
- W223649340 hasConcept C2776276205 @default.
- W223649340 hasConcept C2779012754 @default.
- W223649340 hasConcept C2779825165 @default.
- W223649340 hasConcept C2780450521 @default.
- W223649340 hasConcept C544778455 @default.
- W223649340 hasConcept C7596914 @default.
- W223649340 hasConceptScore W223649340C131779359 @default.
- W223649340 hasConceptScore W223649340C161790260 @default.
- W223649340 hasConceptScore W223649340C178790620 @default.
- W223649340 hasConceptScore W223649340C185592680 @default.
- W223649340 hasConceptScore W223649340C21774173 @default.
- W223649340 hasConceptScore W223649340C21951064 @default.
- W223649340 hasConceptScore W223649340C2776276205 @default.
- W223649340 hasConceptScore W223649340C2779012754 @default.
- W223649340 hasConceptScore W223649340C2779825165 @default.
- W223649340 hasConceptScore W223649340C2780450521 @default.
- W223649340 hasConceptScore W223649340C544778455 @default.
- W223649340 hasConceptScore W223649340C7596914 @default.
- W223649340 hasLocation W2236493401 @default.
- W223649340 hasOpenAccess W223649340 @default.
- W223649340 hasPrimaryLocation W2236493401 @default.
- W223649340 hasRelatedWork W2039450746 @default.
- W223649340 hasRelatedWork W2062649207 @default.
- W223649340 hasRelatedWork W2068896901 @default.
- W223649340 hasRelatedWork W2285423923 @default.
- W223649340 hasRelatedWork W2334950414 @default.
- W223649340 hasRelatedWork W2346305616 @default.
- W223649340 hasRelatedWork W2470185549 @default.
- W223649340 hasRelatedWork W2768445226 @default.
- W223649340 hasRelatedWork W2782545172 @default.
- W223649340 hasRelatedWork W2867980913 @default.
- W223649340 hasRelatedWork W2949267550 @default.
- W223649340 hasRelatedWork W2950291660 @default.
- W223649340 hasRelatedWork W2950493216 @default.
- W223649340 hasRelatedWork W2951431920 @default.
- W223649340 hasRelatedWork W2951875514 @default.
- W223649340 hasRelatedWork W2951929688 @default.
- W223649340 hasRelatedWork W2952271885 @default.
- W223649340 hasRelatedWork W3048733243 @default.
- W223649340 hasRelatedWork W3161916886 @default.
- W223649340 hasRelatedWork W2942237819 @default.
- W223649340 isParatext "false" @default.
- W223649340 isRetracted "false" @default.
- W223649340 magId "223649340" @default.
- W223649340 workType "article" @default.