The Experts below are selected from a list of 285 Experts worldwide ranked by ideXlab platform
Stephen L. Buchwald - One of the best experts on this subject based on the ideXlab platform.
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cuh catalyzed enantioselective alkylation of indole derivatives with ligand controlled regiodivergence
Journal of the American Chemical Society, 2019Co-Authors: Yuxuan Ye, Jinhoon Jeong, Mu-hyun Baik, Stephen L. BuchwaldAbstract:Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral Indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral Indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which Indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)Indoles, as coupling partners. N- or C3-alkylated Indoles are prepared with hig...
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cuh catalyzed enantioselective alkylation of indole derivatives with ligand controlled regiodivergence
Journal of the American Chemical Society, 2019Co-Authors: Yuxuan Ye, Jinhoon Jeong, Mu-hyun Baik, Stephen L. BuchwaldAbstract:Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral Indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral Indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which Indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)Indoles, as coupling partners. N- or C3-alkylated Indoles are prepared with hig...
Min Shi - One of the best experts on this subject based on the ideXlab platform.
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rhodium ii catalyzed intermolecular 3 2 annulation of n vinyl Indoles with n tosyl 1 2 3 triazoles via an aza vinyl rh carbene
Organic chemistry frontiers, 2017Co-Authors: Bo Jiang, Min ShiAbstract:The rhodium(II)-catalyzed annulations of N-vinyl indole derivatives and N-tosyl-1,2,3-triazoles have been developed in this paper, providing a convenient, efficient and straightforward access to synthesize Indoles containing a N-dihydropyrrole in moderate to good yields. Furthermore, the reaction of N-vinyl Indoles with 2.5 equiv. of N-tosyl-1,2,3-triazoles gave C3-functionalized Indoles containing a N-dihydropyrrole in moderate yields after reduction with NaBH3CN in a one-pot manner. This finding gives a new synthetic protocol for the preparation of Indoles containing a N-dihydropyrrole under mild conditions.
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divergent synthesis of indole fused polycycles via rh ii catalyzed intramolecular 3 2 cycloaddition and c h functionalization of indolyltriazoles
Organic chemistry frontiers, 2015Co-Authors: Yongsheng Zhang, Xiangying Tang, Min ShiAbstract:Rh(II)-catalyzed divergent synthesis of polycyclic indolines and azepino[4,5-b]Indoles through intramolecular [3 + 2] cycloaddition and C–H functionalization of Indoles with N-sulfonyl 1,2,3-triazoles is described. The reaction pathways are controlled by the substituent type of indole.
Yuxuan Ye - One of the best experts on this subject based on the ideXlab platform.
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cuh catalyzed enantioselective alkylation of indole derivatives with ligand controlled regiodivergence
Journal of the American Chemical Society, 2019Co-Authors: Yuxuan Ye, Jinhoon Jeong, Mu-hyun Baik, Stephen L. BuchwaldAbstract:Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral Indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral Indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which Indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)Indoles, as coupling partners. N- or C3-alkylated Indoles are prepared with hig...
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cuh catalyzed enantioselective alkylation of indole derivatives with ligand controlled regiodivergence
Journal of the American Chemical Society, 2019Co-Authors: Yuxuan Ye, Jinhoon Jeong, Mu-hyun Baik, Stephen L. BuchwaldAbstract:Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral Indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral Indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which Indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)Indoles, as coupling partners. N- or C3-alkylated Indoles are prepared with hig...
Yanguang Wang - One of the best experts on this subject based on the ideXlab platform.
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3-Alkenylation or 3-alkylation of indole with propargylic alcohols: construction of 3,4-dihydrocyclopenta[b]indole and 1,4-dihydrocyclopenta[b]indole in the presence of different catalysts.
Journal of Organic Chemistry, 2012Co-Authors: Li Zhang, Ping Lu, Yanguang WangAbstract:3-Alkenylation or 3-alkylation of indole with propargylic alcohols could be efficiently controlled by the catalyst. In the presence of triflic acid, 3-alkenylation of indole occurred and a 3,4-dihydrocyclopenta[b]indole skeleton was effectively constructed in moderate to excellent yields via a cascade process. In the presence of Cu(OTf)2, 3-alkylation of indole resulted in the formation of 3-propargylic indole, which could be further converted into 2-iodo-1,4-dihydrocyclopenta[b]Indoles in the presence of N-iodosuccinimide and boron trifluoride etherate. Possible mechanisms related to the 3-alkenylation or 3-alkylation of indole and their extension to the formation of 3,4-dihydrocyclopenta[b]Indoles or 1,4-dihydrocyclopenta[b]Indoles are postulated and discussed.
Thomas R Ward - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of N-Substituted Indoles via Aqueous Ring-Closing Metathesis
Catalysis Letters, 2020Co-Authors: Valerio Sabatino, Dario Staub, Thomas R WardAbstract:We report herein the synthesis of N -substituted Indoles resulting from the ring-closing metathesis of indole precursors bearing N -terminal alkenes. The aqueous metathesis of the indole precursors gave good yields of N -substituted Indoles (up to 72%) with commercial metathesis catalysts and with artificial metalloenzymes based on the biotin-streptavidin technology. Strikingly, the yield of the N -acetylindole increases in presence of a second metathesis substrate. Graphic Abstract
