The Experts below are selected from a list of 213 Experts worldwide ranked by ideXlab platform
Sanggi Lee - One of the best experts on this subject based on the ideXlab platform.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
ChemInform, 2015Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:The rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with various enamino esters affords dihydroimidazoles with a broad functional group tolerance.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
Journal of Organic Chemistry, 2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer.
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From Triazoles to Imidazolines through the Sequential N–H Insertion of α‑Imino Rhodium–Carbenes into β‑Enamino Esters/Enamine–Imine Tautomerization/Conjugate Addition Cascade
2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer
Hyun Ji Jeon - One of the best experts on this subject based on the ideXlab platform.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
ChemInform, 2015Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:The rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with various enamino esters affords dihydroimidazoles with a broad functional group tolerance.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
Journal of Organic Chemistry, 2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer.
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From Triazoles to Imidazolines through the Sequential N–H Insertion of α‑Imino Rhodium–Carbenes into β‑Enamino Esters/Enamine–Imine Tautomerization/Conjugate Addition Cascade
2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer
Sanzhong Luo - One of the best experts on this subject based on the ideXlab platform.
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Redox Property of Enamines
The Journal of organic chemistry, 2019Co-Authors: Dehong Wang, Long Zhang, Sanzhong LuoAbstract:Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary Enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of Enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant Enamines. Spin population analysis disclosed that Enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of Enamines is presented, which would provide guidance in the development of oxidative Enamine catalysis and transformations.
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Catalytic Asymmetric Oxidative Enamine Transformations
ACS Catalysis, 2018Co-Authors: Lihui Zhu, Dehong Wang, Zongbin Jia, Qifeng Lin, Mouxin Huang, Sanzhong LuoAbstract:Enamine catalysis is a prevalent strategy for the functionalization of aldehydes/ketones with electrophiles. Recently, the advent and development of oxidative Enamine catalysis have allowed for the coupling of Enamines with readily available nucleophiles under oxidative conditions, significantly expanding the domain of typical Enamine catalysis. In this perspective, we summarize the recent advances in asymmetric oxidative Enamine catalysis. On the basis of the oxidative strategy, these could be classified as (1) oxidation of nucleophile, (2) oxidation of Enamine via single-electron transfer (SOMO catalysis), and (3) oxidation of Enamine to α,β-unsaturated iminium ion, i.e. oxidative iminium catalysis. These strategies have enabled efficient oxidative functionalizations of aldehydes/ketones with various O-, N-, and C-centered nucleophiles in a highly stereocontrolled manner.
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Catalytic asymmetric Enamine protonation reaction
Organic & biomolecular chemistry, 2018Co-Authors: Long Zhang, Sanzhong LuoAbstract:Enantioselective protonation, delivery of a proton to a carbanion intermediate, is the most straightforward and fundamental method for the preparation of a chiral tertiary carbon stereocenter. Recent efforts for this objective have been realized through Enamine catalysis, which has now become a prominent catalytic strategy enabling a range of fascinating chiral transformations. This review will summarize recent advances in the field of enantioselective Enamine protonation for the synthesis of optically active carbonyl compounds. Dynamic kinetic resolutions of α-substituted carbonyl compounds through Enamine intermediates will be discussed as well.
Youngmee Kim - One of the best experts on this subject based on the ideXlab platform.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
ChemInform, 2015Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:The rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with various enamino esters affords dihydroimidazoles with a broad functional group tolerance.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
Journal of Organic Chemistry, 2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer.
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From Triazoles to Imidazolines through the Sequential N–H Insertion of α‑Imino Rhodium–Carbenes into β‑Enamino Esters/Enamine–Imine Tautomerization/Conjugate Addition Cascade
2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer
Da Jung Jung - One of the best experts on this subject based on the ideXlab platform.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
ChemInform, 2015Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:The rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with various enamino esters affords dihydroimidazoles with a broad functional group tolerance.
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from triazoles to imidazolines through the sequential n h insertion of α imino rhodium carbenes into β enamino esters Enamine imine tautomerization conjugate addition cascade
Journal of Organic Chemistry, 2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer.
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From Triazoles to Imidazolines through the Sequential N–H Insertion of α‑Imino Rhodium–Carbenes into β‑Enamino Esters/Enamine–Imine Tautomerization/Conjugate Addition Cascade
2014Co-Authors: Hyun Ji Jeon, Da Jung Jung, Ju Hyun Kim, Youngmee Kim, Jean Bouffard, Sanggi LeeAbstract:A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N–H insertion of an α-imino rhodium–carbene, followed by Enamine–imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer
