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Journal articles on the topic 'Pentanidium'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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1

Kee, Choon Wee, and Ming Wah Wong. "Pentanidium-Catalyzed Asymmetric Phase-Transfer Conjugate Addition: Prediction of Stereoselectivity via DFT Calculations and Docking Sampling of Transition States, and Origin of Stereoselectivity." Australian Journal of Chemistry 69, no. 9 (2016): 983. http://dx.doi.org/10.1071/ch16225.

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Density functional theory (DFT) study, at the M06–2X/6–311+G(d,p)//M06–2X/6–31G(d,p) level, was carried out to examine the catalytic mechanism and origin of stereoselectivity of pentanidium-catalyzed asymmetric phase-transfer conjugate addition. We employed a hybrid approach by combining automated conformation generation through molecular docking followed by subsequent DFT calculation to locate various possible transition states for the enantioselective conjugate addition. The calculated enantioselectivity (enantiomeric excess), based on the key diastereomeric C–C bond-forming transition states, is in good accord with experimental result. Non-covalent interaction analysis of the key transition states reveals extensive non-covalent interactions, including aromatic interactions, hydrogen bonds, and non-classical C–H⋯O interactions between the pentanidium catalyst and substrates. The origin of stereoselectivity was analysed using a strain-interaction model.
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2

Ma, Ting, Xiao Fu, Choon Wee Kee, Lili Zong, Yuanhang Pan, Kuo-Wei Huang, and Choon-Hong Tan. "Pentanidium-Catalyzed Enantioselective Phase-Transfer Conjugate Addition Reactions." Journal of the American Chemical Society 133, no. 9 (March 9, 2011): 2828–31. http://dx.doi.org/10.1021/ja1098353.

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3

Yang, Yuanyong, Farhana Moinodeen, Willy Chin, Ting Ma, Zhiyong Jiang, and Choon-Hong Tan. "Pentanidium–Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen." Organic Letters 14, no. 18 (September 4, 2012): 4762–65. http://dx.doi.org/10.1021/ol302030v.

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4

Zhou, Shun, Lin Zhang, Chun Li, Yuanhu Mao, Jianta Wang, Ping Zhao, Lei Tang, and Yuanyong Yang. "Pentanidium catalyzed enantioselective hydroperoxidation of 2-oxindole using molecular oxygen." Catalysis Communications 82 (July 2016): 29–31. http://dx.doi.org/10.1016/j.catcom.2016.04.016.

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5

Ma, Ting, Xiao Fu, Choon Wee Kee, Lili Zong, Yuanhang Pan, Kuo-Wei Huang, and Choon-Hong Tan. "ChemInform Abstract: Pentanidium-Catalyzed Enantioselective Phase-Transfer Conjugate Addition Reactions." ChemInform 42, no. 28 (June 16, 2011): no. http://dx.doi.org/10.1002/chin.201128023.

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6

Teng, Bo, Wenchao Chen, Shen Dong, Choon Wee Kee, Dhika Aditya Gandamana, Lili Zong, and Choon-Hong Tan. "Pentanidium- and Bisguanidinium-Catalyzed Enantioselective Alkylations Using Silylamide as Brønsted Probase." Journal of the American Chemical Society 138, no. 31 (August 2016): 9935–40. http://dx.doi.org/10.1021/jacs.6b05053.

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7

Yang, Yuanyong, Farhana Moinodeen, Willy Chin, Ting Ma, Zhiyong Jiang, and Choon-Hong Tan. "ChemInform Abstract: Pentanidium-Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen." ChemInform 44, no. 3 (January 15, 2013): no. http://dx.doi.org/10.1002/chin.201303099.

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8

Zong, Lili, Xu Ban, Choon Wee Kee, and Choon-Hong Tan. "Catalytic Enantioselective Alkylation of Sulfenate Anions to Chiral Heterocyclic Sulfoxides Using Halogenated Pentanidium Salts." Angewandte Chemie 126, no. 44 (September 10, 2014): 12043–47. http://dx.doi.org/10.1002/ange.201407512.

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9

Zong, Lili, Xu Ban, Choon Wee Kee, and Choon-Hong Tan. "Catalytic Enantioselective Alkylation of Sulfenate Anions to Chiral Heterocyclic Sulfoxides Using Halogenated Pentanidium Salts." Angewandte Chemie International Edition 53, no. 44 (September 10, 2014): 11849–53. http://dx.doi.org/10.1002/anie.201407512.

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10

Ren, Jingyun, Xu Ban, Xin Zhang, Siu Min Tan, Richmond Lee, and Choon‐Hong Tan. "Kinetic and Dynamic Kinetic Resolution of Racemic Tertiary Bromides by Pentanidium‐Catalyzed Phase‐Transfer Azidation." Angewandte Chemie International Edition 59, no. 23 (March 24, 2020): 9055–58. http://dx.doi.org/10.1002/anie.202000138.

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11

Ren, Jingyun, Xu Ban, Xin Zhang, Siu Min Tan, Richmond Lee, and Choon‐Hong Tan. "Kinetic and Dynamic Kinetic Resolution of Racemic Tertiary Bromides by Pentanidium‐Catalyzed Phase‐Transfer Azidation." Angewandte Chemie 132, no. 23 (March 24, 2020): 9140–43. http://dx.doi.org/10.1002/ange.202000138.

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12

Zong, Lili, Xu Ban, Choon Wee Kee, and Choon-Hong Tan. "ChemInform Abstract: Catalytic Enantioselective Alkylation of Sulfenate Anions to Chiral Heterocyclic Sulfoxides Using Halogenated Pentanidium Salts." ChemInform 46, no. 13 (March 2015): no. http://dx.doi.org/10.1002/chin.201513126.

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13

Zong, Lili, and Choon-Hong Tan. "Phase-Transfer and Ion-Pairing Catalysis of Pentanidiums and Bisguanidiniums." Accounts of Chemical Research 50, no. 4 (April 5, 2017): 842–56. http://dx.doi.org/10.1021/acs.accounts.6b00604.

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14

Zong, Lili, Shubo Du, Kek Foo Chin, Chao Wang, and Choon-Hong Tan. "Enantioselective Synthesis of Quaternary Carbon Stereocenters: Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Pentanidiums." Angewandte Chemie 127, no. 32 (July 14, 2015): 9522–25. http://dx.doi.org/10.1002/ange.201503844.

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15

Zong, Lili, Shubo Du, Kek Foo Chin, Chao Wang, and Choon-Hong Tan. "Enantioselective Synthesis of Quaternary Carbon Stereocenters: Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Pentanidiums." Angewandte Chemie International Edition 54, no. 32 (July 15, 2015): 9390–93. http://dx.doi.org/10.1002/anie.201503844.

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16

Zong, Lili, Shubo Du, Kek Foo Chin, Chao Wang, and Choon-Hong Tan. "ChemInform Abstract: Enantioselective Synthesis of Quaternary Carbon Stereocenters: Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Pentanidiums." ChemInform 46, no. 48 (November 12, 2015): no. http://dx.doi.org/10.1002/chin.201548130.

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17

Tan, Choon-Hong, and Benjamin List. "Cluster Preface: Asymmetric Brønsted Base Catalysis." Synlett 28, no. 11 (June 20, 2017): 1270–71. http://dx.doi.org/10.1055/s-0036-1590548.

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Choon-Hong Tan is a professor at the Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore. He received his BSc (Hons) First Class from the National University of Singapore (NUS) and his Phd from the University of Cambridge. He underwent postdoctoral training at the Department of Chemistry and Chemical Biology, Harvard University and the Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School. He began his independent career at the Department of Chemistry, National University of Singapore in 2003. Choon Hong has focused on the development of organocatalytic Brønsted base reactions that can be catalyzed with chiral guanidines. He has also demonstrated that pentanidiums (conjugated guanidiniums) are efficient phase-transfer catalysts. Recently, he described the use of chiral organic cations such as bisguanidiniums to modulate and activate anionic metallic salts. Benjamin List has been a director at the Max-Planck-Institut für Kohlenforschung since 2005. He obtained his Ph.D. in 1997 (Frankfurt). From 1997 until 1998 he conducted postdoctoral research at The Scripps Research Institute in La Jolla (USA) and became an assistant professor there in January 1999. In 2003 he joined the Max-Planck-Institut für Kohlenforschung. He has been an honorary professor at the University of Cologne since 2004. Ben List’s research focuses on organic synthesis and catalysis. He has contributed fundamental concepts to chemical synthesis including aminocatalysis, enamine catalysis, and asymmetric-counteranion-directed catalysis (ACDC). His latest work deals with chiral counteranions in asymmetric catalysis. This remarkably general strategy for asymmetric synthesis has recently found widespread use in organocatalysis, transition-metal catalysis, and Lewis acid catalysis.
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18

"Pentanidium-Type Chiral Phase-Transfer Catalysts." Synfacts 2011, no. 05 (April 15, 2011): 0556. http://dx.doi.org/10.1055/s-0030-1259852.

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19

Ban, Xu, Yifan Fan, Tuan-Khoa Kha, Richmond Lee, Choon Wee Kee, Zhiyong Jiang, and Choon-Hong Tan. "Pentanidium-Catalyzed Direct Assembly of Vicinal All-Carbon Quaternary Stereocenters through C(sp 3 )-C(sp 3 ) Bond Formation." CCS Chemistry, June 26, 2021, 1–21. http://dx.doi.org/10.31635/ccschem.021.202101013.

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