2014
DOI: 10.1002/ange.201309126
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Atom‐Economic, Regiodivergent, and Stereoselective Coupling of Imidazole Derivatives with Terminal Allenes

Abstract: New Rh‐ and Pd‐catalyzed regiodivergent and stereoselective intermolecular coupling reactions of imidazole derivatives with mono‐substituted allenes are herein reported. Using a RhI/Josiphos system, perfect regioselectivities and high enantiomeric excess were obtained, while a PdII/dppf system gave linear products with high regioselectivities and high E/Z selectivities. This method permits the atom economic synthesis of valuable branched and linear allylic imidazole derivatives.

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Cited by 45 publications
(34 citation statements)
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“…13 C NMR (101 MHz, CDCl 3 ) δ 159. 8, 159.7, 141.0, 139.6, 137.4, 133.6, 129.8, 129.5, 128.6, 127.4, 119.6, 119.4, 113.9, 113.3, 113.2, 111.9, 105.6, 67.4, 13 C NMR (101 MHz, CDCl 3 ) δ 156. 9, 156.7, 139.4, 129.3, 129.0, 128.8, 128.4, 128.1, 128.0, 127.7, 127.4, 125.4, 120.8, 120.…”
Section: (E)-1-(13-bis(3-methoxyphenyl)allyl)-1h-pyrazole (3 D)mentioning
confidence: 99%
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“…13 C NMR (101 MHz, CDCl 3 ) δ 159. 8, 159.7, 141.0, 139.6, 137.4, 133.6, 129.8, 129.5, 128.6, 127.4, 119.6, 119.4, 113.9, 113.3, 113.2, 111.9, 105.6, 67.4, 13 C NMR (101 MHz, CDCl 3 ) δ 156. 9, 156.7, 139.4, 129.3, 129.0, 128.8, 128.4, 128.1, 128.0, 127.7, 127.4, 125.4, 120.8, 120.…”
Section: (E)-1-(13-bis(3-methoxyphenyl)allyl)-1h-pyrazole (3 D)mentioning
confidence: 99%
“…Light yellow viscous oily liquid; 165.5 mg, 87% isolated yield; 1 H NMR (400 MHz, CDCl 3 ) δ 7.52 (dd, J = 50.2, 2.1 Hz, 2H), 6H),6.56 (dd,J = 15.8,6.7 Hz,1H),2H),6.10 (d,J = 6.8 Hz,1H),12H). 13 C NMR (101 MHz, CDCl 3 ) δ 149. 10, 149.06, 148.9, 148.7, 139.5, 133.1, 132.0, 129.0, 128.5, 125.4, 120.0, 119.6, 111.0, 110.9, 110.5, 108.9, 105.5, 67.3, 55.82, 55.80, 55.77…”
Section: (E)-1-(13-bis(34-dimethoxyphenyl)allyl)-1h-pyrazole (3 F)mentioning
confidence: 99%
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“…1C ) ( 28 , 29 ). Despite extensive efforts dedicated to developing efficient methods for aminative functionalization of allenes, there are still great challenges owing to regio- and stereocontrol as well as reactivity issues: (i) The unique accumulated diene structural units have greatly limited the selective activation of the two carbon-carbon double bonds of allenes ( 30 ). (ii) Efficient selective synthesis of Z -allylamines remains a challenging task for their thermodynamic instability ( 31 34 ).…”
Section: Introductionmentioning
confidence: 99%