2018
DOI: 10.1002/adsc.201701450
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Abstract: Owing to the dehydrogenative rearomatization of hydrogenation product and poisoning effect of nitrogen atom, asymmetric hydrogenation of polycyclic nitrogen‐containing heteroaromatics is still a great challenge. Herein, through in situ protection of hydrogenation products with acetic anhydride to inhibit rearomatization and poisoning effect, a novel iridium‐catalyzed enantioselective hydrogenation of polycyclic nitrogen‐containing heteroaromatics – pyrrolo/indolo[1,2‐a]quinoxalines and phenanthridines – has be… Show more

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Cited by 24 publications
(13 citation statements)
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“…5,6-Dihydrophenanthridines with diverse α substituent patterns are present in a number of bioactive molecules possessing a wide range of pharmacological activities . However, surprisingly few catalytic enantioselective methods to access enantiopure compounds have been reported, and each method is typically suitable for a specific substituent pattern of functionalities in the α position as well as the heterocyclic skeleton . Therefore, dehydrogenative KR of 5,6-dihydrophenanthridine 1a under air at ambient temperature was selected as the model reaction for the search of chiral iron catalyst systems (Table ).…”
Section: Results and Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…5,6-Dihydrophenanthridines with diverse α substituent patterns are present in a number of bioactive molecules possessing a wide range of pharmacological activities . However, surprisingly few catalytic enantioselective methods to access enantiopure compounds have been reported, and each method is typically suitable for a specific substituent pattern of functionalities in the α position as well as the heterocyclic skeleton . Therefore, dehydrogenative KR of 5,6-dihydrophenanthridine 1a under air at ambient temperature was selected as the model reaction for the search of chiral iron catalyst systems (Table ).…”
Section: Results and Discussionmentioning
confidence: 99%
“…Other common functionalities, including alkyl ( 1q – 1s ), benzyl ( 1t ), and phenethyl ( 1u ), at the α position were also well tolerated, thus demonstrating the capacity of the dehydrogenative KR strategy for asymmetric access to diversely functionalized molecules . Notably, previously reported catalytic asymmetric methods are limited to either α-aryl- or α-alkyl-substituted 5,6-dihydrophenanthridines …”
Section: Results and Discussionmentioning
confidence: 99%
“…Structural variations of the ligand include alteration of P -substitution and modifications of the phenyl backbone, including the synthesis of supramolecular chiral ligands appended with crown ethers that induce strong complexation between the ligand and alkali cations . Since 2011, the combination of iridium and biaryl bisphosphine ligands has been extensively studied by Zhou, Agbossou-Niedercorn, and Mashima in the asymmetric hydrogenation of heteroarenes, including quinolines, isoquinolines, , quinoxalines, , pyridines, pyrazines, and benzoxazines . Iodine, chloroformates, amines, and Brønsted acids are common activating reagents for enhancing catalytic activity of these heterocyclic substrates.…”
Section: Iridium-catalyzed Asymmetric Hydrogenationmentioning
confidence: 99%
“…Additionally, phenanthridine-type substrates were found to be compatible and gave the corresponding amine products in 62-98% ee. 16 In a study by Verdaguer et al, four diastereomers of the ligand in complex 9a were synthesised alongside their respective complexes. AH of acetophenone-N-methyl imines with the complexes gave products in low enantioselectivities of 9-71% ee.…”
Section: Organic Chemistry Frontiers Reviewmentioning
confidence: 99%