- One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis
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A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.
- Henry, Martyn C.,McGrory, Rochelle,Faggyas, Réka J.,Mostafa, Mohamed A. B.,Sutherland, Andrew
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p. 4629 - 4639
(2019/05/17)
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- Perylenequinone natural products: Total syntheses of the diastereomers (+)-phleichrome and (+)-calphostin D by assembly of centrochiral and axial chiral fragments
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(Chemical Equation Presented) The first total synthesis of (+)-calphostin D and the total synthesis of (+)-phleichrome are outlined. The convergent syntheses utilize an enantiopure biaryl common intermediate, which is formed via an enantioselective cataly
- Morgan, Barbara J.,Mulrooney, Carol A.,O'Brien, Erin M.,Kozlowski, Marisa C.
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supporting information; experimental part
p. 30 - 43
(2010/04/26)
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- Dynamic stereochemistry transfer in a transannular aldol reaction: Total synthesis of hypocrellin A
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(Chemical Equation Presented) A dynamic approach: The key step in the total synthesis of hypocrellin A involves a potentially biomimetic 1,8-diketone aldol reaction, which constructs the seven-membered ring. The helical configuration is established first
- O'Brien, Erin M.,Morgan, Barbara J.,Kozlowski, Marisa C.
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supporting information; experimental part
p. 6877 - 6880
(2009/04/07)
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- On the Synthesis of Tiliacora Alkaloids, II: Synthesis of the Asymmetrical Biphenyl Derivative
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The biphenyl derivatives S-1 and S-3 were obtained by mixed Ullmann reaction of the phenylacetic esters 3, 4 and 5.Because they contain selectively removable protective groups for the carboxyl functions, S-1 and S-3 are proper intermediates for the constitution selective reaction with the former described asymmetrical dibenzo-1,4-dioxin derivative K.
- Pachaly, Peter,Schaefer, Michael
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p. 483 - 487
(2007/10/02)
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