Discovery of an iridacycle catalyst with improved reactivity and enantioselectivity in the hydrogenation of dialkyl ketimines

York Schramm, Fabiola Barrios-Landeros and Andreas Pfaltz

Chem. Sci., 2013, 4, 2760
DOI: 10.1039/c3sc50587a

Electronic effects of triarylphosphines in metal-free hydrogen activation: a kinetic and computational study

Lutz Greb, Sebastian Tussing, Birgitta Schirmer, Pascual Oña-Burgos, Karl Kaupmees, Märt Lõkov, Ivo Leito, Stefan Grimme and Jan Paradies

Chem. Sci., 2013, 4, 2788
DOI: 10.1039/c3sc50347j

Au/TiO2catalyzed reductive amination of aldehydes and ketones using formic acid as reductant

Shengzong Liang, Paige Monsen, Gerald B. Hammond and Bo Xu

Org. Chem. Front., 2016, 3, 505
DOI: 10.1039/C5QO00439J

Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3′-substituents in Brønsted acid catalysis

Kerstin Rothermel, Maxime Melikian, Johnny Hioe, Julian Greindl, Johannes Gramüller, Matej Žabka, Nils Sorgenfrei, Thomas Hausler, Fabio Morana and Ruth M. Gschwind

Chem. Sci., 2019, 10, 10025
DOI: 10.1039/C9SC02342A

Prediction of suitable catalyst by 1H NMR: asymmetric synthesis of multisubstituted biaryls by chiral phosphoric acid catalyzed asymmetric bromination

Keiji Mori, Yuki Ichikawa, Manato Kobayashi, Yukihiro Shibata, Masahiro Yamanaka and Takahiko Akiyama

Chem. Sci., 2013, 4, 4235
DOI: 10.1039/c3sc52142g

Brønsted acid catalysis – the effect of 3,3′-substituents on the structural space and the stabilization of imine/phosphoric acid complexes

Maxime Melikian, Johannes Gramüller, Johnny Hioe, Julian Greindl and Ruth M. Gschwind

Chem. Sci., 2019, 10, 5226
DOI: 10.1039/C9SC01044K

Recent advances in organocatalytic enantioselective transfer hydrogenation

Ana Maria Faísca Phillips and Armando J. L. Pombeiro

Org. Biomol. Chem., 2017, 15, 2307
DOI: 10.1039/C7OB00113D

Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking

Keiji Mori, Ayaka Miyake and Takahiko Akiyama

Chem. Commun., 2015, 51, 16107
DOI: 10.1039/C5CC05508C

Synthetic methods: part (ii) oxidation and reduction methods

Yi Sing Gee, Kamelia Fathy Abd El Kader and Christopher J. T. Hyland

Annu. Rep. Prog. Chem., Sect. B: Org. Chem., 2013, 109, 103
DOI: 10.1039/c3oc90011h

Biomimetic Asymmetric Reduction Based on the Regenerable Coenzyme NAD(P)H Models

Mu-Wang Chen, Bo Wu, Zheng Liu and Yong-Gui Zhou

Acc. Chem. Res., 2023, 56, 2096
DOI: 10.1021/acs.accounts.3c00129

ChemInform Abstract: Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor.

Kodai Saito and Takahiko Akiyama

ChemInform, 2012, 43
DOI: 10.1002/chin.201236025

Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline As a Deuterium Donor: Synthesis of Optically Active Deuterated Amines

Tsubasa Sakamoto, Keiji Mori and Takahiko Akiyama

Org. Lett., 2012, 14, 3312
DOI: 10.1021/ol3012869

Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination

Kyung-Hee Kim, Chun-Young Lee and Cheol-Hong Cheon

J. Org. Chem., 2015, 80, 6367
DOI: 10.1021/acs.joc.5b00812

Benzothiazoline: Versatile Hydrogen Donor for Organocatalytic Transfer Hydrogenation

Chen Zhu, Kodai Saito, Masahiro Yamanaka and Takahiko Akiyama

Acc. Chem. Res., 2015, 48, 388
DOI: 10.1021/ar500414x

Modular Enantioselective Synthesis of cis-Cyclopropanes through Self-Sensitized Stereoselective Photodecarboxylation with Benzothiazolines

Matteo Costantini and Abraham Mendoza

ACS Catal., 2021, 11, 13312
DOI: 10.1021/acscatal.1c03949

Bifunctional Pincer Catalysts for Chemoselective Transfer Hydrogenation and Related Reactions

Shirel Cohen, Alexey N. Bilyachenko and Dmitri Gelman

Eur J Inorg Chem, 2019, 2019, 3203
DOI: 10.1002/ejic.201801486

Synthesis and Properties of Arsenic(III)-Reactive Coumarin-Appended Benzothiazolines: A New Approach for Inorganic Arsenic Detection

Vivian C. Ezeh and Todd C. Harrop

Inorg. Chem., 2013, 52, 2323
DOI: 10.1021/ic301730z

Diastereoselective Reductive Etherification Via High-Throughput Experimentation: Access to Pharmaceutically Relevant Alkyl Ethers

Jiantao Fu, Zoe Vaughn, Andrew F. Nolting, Qi Gao, Dexi Yang, Christopher H. Schuster and Dipannita Kalyani

J. Org. Chem., 2023, 88, 13454
DOI: 10.1021/acs.joc.3c00822

Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control

Kodai Saito, Hiromitsu Miyashita, Yui Ito, Masahiro Yamanaka and Takahiko Akiyama

Org. Lett., 2020, 22, 3128
DOI: 10.1021/acs.orglett.0c00887

Chiral β‐Lactam Synthesis through the Enantioselective Reduction of Iminocyclobutenones and the Thermal Rearrangement of Aminocyclobutenones

Iwao Hachiya, Akinori Ito and Makoto Shimizu

Asian J Org Chem, 2014, 3, 614
DOI: 10.1002/ajoc.201402005

DFT Study of the Mechanism and Origin of Enantioselectivity in Chiral BINOL-Phosphoric Acid Catalyzed Transfer Hydrogenation of Ketimine and α-Imino Ester Using Benzothiazoline

Yukihiro Shibata and Masahiro Yamanaka

J. Org. Chem., 2013, 78, 3731
DOI: 10.1021/jo4002195

A Practical Guide for Predicting the Stereochemistry of Bifunctional Phosphoric Acid Catalyzed Reactions of Imines

Jolene P. Reid, Luis Simón and Jonathan M. Goodman

Acc. Chem. Res., 2016, 49, 1029
DOI: 10.1021/acs.accounts.6b00052

Enantioselective Transfer Hydrogenation of Difluoromethyl Ketimines Using Benzothiazoline as a Hydrogen Donor in Combination with a Chiral Phosphoric Acid

Tsubasa Sakamoto, Kosaku Horiguchi, Kodai Saito, Keiji Mori and Takahiko Akiyama

Asian J Org Chem, 2013, 2, 943
DOI: 10.1002/ajoc.201300174

Chiral Phosphoric Acid-Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines

Kodai Saito, Yukihiro Shibata, Masahiro Yamanaka and Takahiko Akiyama

J. Am. Chem. Soc., 2013, 135, 11740
DOI: 10.1021/ja406004q

Asymmetric Reductive Amination with Pinacolborane Catalyzed by Chiral SPINOL Borophosphates

Zhenwei Wu, Hualing He, Minglei Chen, Linfei Zhu, Weitao Zheng, Yang Cao and Jon C. Antilla

Org. Lett., 2022, 24, 9436
DOI: 10.1021/acs.orglett.2c03866

Chiral Phosphoric‐Acid‐Catalyzed Transfer Hydrogenation of Ethyl Ketimine Derivatives by Using Benzothiazoline

Kodai Saito, Kosaku Horiguchi, Yukihiro Shibata, Masahiro Yamanaka and Takahiko Akiyama

Chemistry A European J, 2014, 20, 7616
DOI: 10.1002/chem.201402763

Asymmetric Organocatalytic Tandem Cyclization/Transfer Hydrogenation: A Synthetic Strategy for Enantioenriched Nitrogen Heterocycles

Feng Shi, Wei Tan, Hong‐Hao Zhang, Mei Li, Qin Ye, Guan‐Hua Ma, Shu‐Jiang Tu and Guigen Li

Adv Synth Catal, 2013, 355, 3715
DOI: 10.1002/adsc.201300576

Asymmetric Transfer Hydrogenation of Ketimines by Indoline as Recyclable Hydrogen Donor

Kodai Saito, Hiromitsu Miyashita and Takahiko Akiyama

Org. Lett., 2014, 16, 5312
DOI: 10.1021/ol502486f

Asymmetric Reductive Amination in Organocatalysis and Biocatalysis

Tingting Li, Qian Zhou, Fanjing Meng, Wenhui Cui, Qian Li, Jiang Zhu and Yang Cao

Eur J Org Chem, 2023, 26
DOI: 10.1002/ejoc.202300507

Molecular iodine catalyzed transfer hydrogenation: reduction of aldimines, ketimines, and α-imino esters

Prabhakar Bachu, Chen Zhu and Takahiko Akiyama

Tetrahedron Letters, 2013, 54, 3977
DOI: 10.1016/j.tetlet.2013.05.071

4,5-Dihydropyrrolo[1,2-a]quinoxalines: A Tunable and Regenerable Biomimetic Hydrogen Source

Zhang-Pei Chen, Mu-Wang Chen, Ran-Ning Guo and Yong-Gui Zhou

Org. Lett., 2014, 16, 1406
DOI: 10.1021/ol500176v

Chiral SPINOL‐Derived Borophosphate‐Catalyzed Asymmetric 1,4‐Reduction of Exocyclic α,β‐Unsaturated Ketones

Wenhui Cui, Fanjing Meng, Zengfeng Zhang, Zhuting Han and Yang Cao

Adv Synth Catal, 2025, 367
DOI: 10.1002/adsc.202401008

Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

Isabelle Aillaud, David M. Barber, Amber L. Thompson and Darren J. Dixon

Org. Lett., 2013, 15, 2946
DOI: 10.1021/ol401039h

Selecting Chiral BINOL‐Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity

Jolene P. Reid and Jonathan M. Goodman

Chemistry A European J, 2017, 23, 14248
DOI: 10.1002/chem.201702019

Development and Recent Progress in the Chiral Brønsted Acid Catalyst

Takahiko Akiyama

J. Syn. Org. Chem., Jpn., 2017, 75, 410
DOI: 10.5059/yukigoseikyokaishi.75.410

Chiral Diselenophosphoric Acids for Ion Pair Catalysis: A Novel Approach to Enhance Both Proton Donating and Proton Accepting Properties

Johannes Eder, Alexander S. Antonov, Elena Yu. Tupikina and Ruth M. Gschwind

Chemistry A European J, 2024, 30
DOI: 10.1002/chem.202401793

Asymmetric Synthesis of α-Amino Ketones by Brønsted Acid Catalysis

Wei Wen, Yu Zeng, Li-Yu Peng, Li-Na Fu and Qi-Xiang Guo

Org. Lett., 2015, 17, 3922
DOI: 10.1021/acs.orglett.5b01972

Additive‐Free Transfer Hydrogenative Direct Asymmetric Reductive Amination Using a Chiral Pyridine‐Derived Half‐Sandwich Catalyst

Yuan Gao, Zhijun Wang, Xinyu Zhang, Min Zhao, Shuai Zhang, Chao Wang, Liang Xu and Pengfei Li

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202303709

Eosin Y catalyzed visible light mediated aerobic photo-oxidative cleavage of the C–C double bond of styrenes

Atul K. Singh, Ruchi Chawla and Lal Dhar S. Yadav

Tetrahedron Letters, 2015, 56, 653
DOI: 10.1016/j.tetlet.2014.11.141

Addition and Correction to Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates

Dixit Parmar, Erli Sugiono, Sadiya Raja and Magnus Rueping

Chem. Rev., 2017, 117, 10608
DOI: 10.1021/acs.chemrev.7b00197

Remarkable Differences in Reactivity between Benzothiazoline and Hantzsch Ester as a Hydrogen Donor in Chiral Phosphoric Acid Catalyzed Asymmetric Reductive Amination of Ketones

Kyung‐Hee Kim, Takahiko Akiyama and Cheol‐Hong Cheon

Chemistry An Asian Journal, 2016, 11, 274
DOI: 10.1002/asia.201501020

The Development of Organocatalytic Asymmetric Reduction of Carbonyls and Imines Using Silicon Hydrides

Wenchao Chen, Choon‐Hong Tan, Hong Wang and Xinyi Ye

Eur J Org Chem, 2021, 2021, 3091
DOI: 10.1002/ejoc.202100394

Chiral Brønsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane

Vladislav Skrypai, Sami E. Varjosaari, Fawwaz Azam, Thomas M. Gilbert and Marc J. Adler

J. Org. Chem., 2019, 84, 5021
DOI: 10.1021/acs.joc.8b03073

Visible‐Light‐Induced Difluoropropargylation Reaction with Benzothiazoline as a Reductant

Jingzhi Chen, Wenhao Huang, Ying Li and Xu Cheng

Adv Synth Catal, 2018, 360, 1466
DOI: 10.1002/adsc.201800066

Additive‐Free Transfer Hydrogenative Direct Asymmetric Reductive Amination Using a Chiral Pyridine‐Derived Half‐Sandwich Catalyst

Yuan Gao, Zhijun Wang, Xinyu Zhang, Min Zhao, Shuai Zhang, Chao Wang, Liang Xu and Pengfei Li

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202303709

Cooperative Catalysis: Combining an Achiral Metal Catalyst with a Chiral Brønsted Acid Enables Highly Enantioselective Hydrogenation of Imines

Weijun Tang, Steven Johnston, Chaoqun Li, Jonathan A. Iggo, John Bacsa and Jianliang Xiao

Chemistry A European J, 2013, 19, 14187
DOI: 10.1002/chem.201302437

Theoretical Study on the Acidities of Chiral Phosphoric Acids in Dimethyl Sulfoxide: Hints for Organocatalysis

Chen Yang, Xiao-Song Xue, Jia-Lu Jin, Xin Li and Jin-Pei Cheng

J. Org. Chem., 2013, 78, 7076
DOI: 10.1021/jo400915f

Chiral phosphoric acid catalyzed asymmetric hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones

Jian-Qing Zhou, Wei-Jian Sheng, Jian-Hong Jia, Qing Ye, Jian-Rong Gao and Yi-Xia Jia

Tetrahedron Letters, 2013, 54, 3082
DOI: 10.1016/j.tetlet.2013.03.138

Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid

Kosaku Horiguchi, Eri Yamamoto, Kodai Saito, Masahiro Yamanaka and Takahiko Akiyama

Chemistry A European J, 2016, 22, 8078
DOI: 10.1002/chem.201601611

Asymmetric Synthesis of Tetrahydro-β-carbolines via Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation Reaction

Qin Yin, Shou-Guo Wang and Shu-Li You

Org. Lett., 2013, 15, 2688
DOI: 10.1021/ol400995c

Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates

Dixit Parmar, Erli Sugiono, Sadiya Raja and Magnus Rueping

Chem. Rev., 2014, 114, 9047
DOI: 10.1021/cr5001496

New potential of the reductive alkylation of amines

K N Gusak, Zh V Ignatovich and E V Koroleva

Russ. Chem. Rev., 2015, 84, 288
DOI: 10.1070/RCR4443