Tanaka Unit Publications

 

2023

Chavan, S. S.; Saze, H.; Tanaka, F. Chemical modification of peptides and proteins using spirooxindole oxirane derivatives. Adv. Synth. Catal. 2023, 365, 2171-2176, doi: 10.1002/adsc.202300578.
URL: https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202300578

Garg, Y.; Osborne, J.; Vasylevskyi, S.; Velmurugan, N.; Tanaka, F. 1,3-Diamine-derived catalysts: Design, synthesis, and the use in enantioselective Mannich reactions of ketones. J. Org. Chem. 2023, 88, 11096-11101, doi: 10.1021/acs.joc.3c01051.
URL: https://pubs.acs.org/doi/full/10.1021/acs.joc.3c01051

Sohail, M.; Tanaka, F. Limiting the loading of reactant 1,3-cyclohexanedione enables the use of less catalyst. J. Org. Chem. 2023, 88, 10277-10281, doi: 10.1021/acs.joc.3c00838.
URL: https://pubs.acs.org/doi/full/10.1021/acs.joc.3c00838

Bethi, V.; Bakhtawar, S.; Rupanawar, R. D.; Tanaka, F. Selective vinylogous aldol reactions of β-methyl-substituted cyclic enones with isatins catalyzed by DBU and Pyrrolidine to afford 3-substituted 3-hydroxyoxindoles. Asian J. Org. Chem. 2023, 12, e202300193, doi: 10.1002/ajoc.202300193.
URL: https://onlinelibrary.wiley.com/doi/full/10.1002/ajoc.202300193

2022

Sohail, M.; Tanaka, F. Synthesis of functionalized spirooxindole polycycles: Use of cyclic 1,3-diones as reactants or as condition-tuning molecules. Synlett 2023, 34, doi 10.1055/a-2061-0855.
URL: https://www.thieme-connect.com/products/ejournals/html/10.1055/a-2061-0855

Tanaka, F. Amines as catalysts: dynamic features and kinetic control of catalytic asymmetric chemical transformations to form C-C bonds and complex molecules. The Chemical Record 2023, 23, e202200207, doi 10.1002/tcr.202200207.
URL: https://onlinelibrary.wiley.com/doi/full/10.1002/tcr.202200207

Bethi, V.; Tanaka, F. Organocatalytic enantioselective γ-position-selective Mannich reactions of β-ketocarbonyl derivatives. Org. Lett. 2022, 24, 6711-6715, doi: 10.1021/acs.orglett.2c02433.
URL: https://pubs.acs.org/doi/full/10.1021/acs.orglett.2c02433

Aher, R. D.; Ishikawa, A.; Yamanaka, M.; Tanaka, F. Catalytic Enantioselective construction of decalin derivatives by dynamic kinetic desymmetrization of C2-symmetric derivatives through aldol-aldol annulation. J. Org. Chem. 2022, 87, 8151-8157, doi: 10.1021/acs.joc.2c00889.
URL: https://pubs.acs.org/doi/full/10.1021/acs.joc.2c00889
URL: https://pubs.acs.org/articlesonrequest/AOR-MD3RUK7QPZFDIYFEDJMY

2021

Mondal, S.; Aher, R. D.; Bethi, V.; Lin, Y.-J.; Taniguchi, T.; Monde, K.; Tanaka, F. Control of reactions of pyruvates by catalysts: Direct enantioselective Mannich reactions of pyruvates catalyzed by amine-based catalyst systems. Org. Lett. 2022, 24, 1853-1858, doi: 10.1021/acs.orglett.2c00436.
URL: https://pubs.acs.org/doi/10.1021/acs.orglett.2c00436
URL: https://pubs.acs.org/articlesonrequest/AOR-VHITTB5NWJZHMEIIPEZV

Fujioka, T.; Numoto, N.; Akama, H.; Shilpa, K.; Oka, M.; Roy, P. K.; Krishna, Y.; Ito, N.; Baker, D.; Oda, M.; Tanaka, F. Varying the directionality of protein catalysts for aldol and retro-aldol reactions. ChemBioChem 2022, 23, e202100435, doi: 10.1002/cbic.202100435.
URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.202100435

Pasha, M.; Tanaka, F. Organocatalytic diastereo- and enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyranes. Org. Biomol. Chem. 2021, 19, 9242-9250, doi: 10.1039/D10B01844B.
URL: https://pubs.rsc.org/en/content/articlelanding/2021/ob/d1ob01844b

Sohail, M.; Tanaka F.  Dynamic kinetic asymmetric transformation of racemic diastereomers: Diastereo- and enantioconvergent Michael-Henry reactions to afford ppirooxindoles bearing furan-fused rings.  Angew. Chem. Int. Ed. 2021, 60, 21256-21260, doi: 10.1002/anie.202108734. (German Edition: Angew. Chem. 2021, 133, 21426-21430, doi: 10.1002/ange.202108734)
URL: https://onlinelibrary.wiley.com/doi/10.1002/anie.202108734

2020

Krishna, Y.; Tanaka, F. Intramolecular Formal [4+2] cycloadditions: Synthesis of spiro isoindolinone derivatives and related molecules. Org. Lett. 2021, 23,1874-1879, doi: 10.1021/acs.orglett1c00283.
URL: https://pubs.acs.org/doi/full/10.1021/acs.orglett.1c00283

Garg, Y.; Tanaka, F. Enantioselective direct anti-selective Mannich-type reactions catalyzed by 3-pyrrolidinecarboxylic acid in the presence of potassium carbonate: Addition of potassium carbonate improves enantioselectivities. Org. Lett. 2020, 22, 4542-4546, doi: 10.1021/acs.orglett.0c01561.
URL: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.0c01561

Pasha, M.; Tanaka, F. Catalytic enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones: Synthesis of tetrahydropyranones. Heterocycles 2021, 103, 198-204, doi: 10.3987/COM-20-S(K)22.
URL: https://www.heterocycles.jp/newlibrary/libraries/prepress
(then, left side, using Quick search" with doi)
URL (OIST repository): https://oist.repo.nii.ac.jp/records/1918

2019

Maram, L.; Tanaka, F. Switching electrophile intermediates to nucleophiles: Michael and oxa-Diels-Alder reactions to afford polyoxy-functionalized piperidine derivatives with tetrasubstituted carbon. Org. Lett. 2020, 22, 2751-2755, doi: 10.1021/acs.orglett.0c00735.
URL: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.0c00735

Zhang, D.; Chen, Y.; Cai, H.; Yin, L.; Zhong, J.; Man, J.; Zhang, Q.-F.; Bethi, V.; Tanaka F. Direct catalytic asymmetric synthesis of oxindole-derived d-hydroxy-b-ketoesters by aldol reactions. Org. Lett. 2020, 22, 6-10, doi: 10.1021/acs.orglett.9b03527.
URL: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b03527

Sohail, M.; Tanaka F. Control of chemical reactions using molecules that buffer non-aqueous solutions.  Chem. Eur. J. 2020, 26, 222-229, doi: 10.1002/chem.201903552.
URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201903552

Krishna, Y.; Shilpa, K.; Tanaka, F. Intramolecular Mannich and Michael annulation reactions of lactam derivatives bearing enals to afford bicyclic N-heterocycles.  Org. Lett. 2019, 21, 8444-8448, doi: 10.1021/acs.orglett.9b03210.
URL: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b03210

Pasha, M.; Sohail, M.; Tanaka F. Intramolecular oxa-Michael reactions of aldols generated from enones and isatins to afford spirooxindole tetrahydropyrans.  Heterocycles 2020, 101, 339-346, doi: 10.3987/COM-19-S(F)26.
URL: https://www.heterocycles.jp/newlibrary/libraries/journal/101/1
(then, left side, using "Quick search" with volume and page or doi)
URL (OIST repository): https://oist.repo.nii.ac.jp/records/1177

Sohail, M.; Tanaka F. Dynamic stereoselective annulation via aldol-oxacyclization cascade reaction to afford spirooxindole pyran polycycles.  Communications Chemistry 2019, 2, article number 73, doi: 10.1038/s42004-019-0177-5.
URL: https://www.nature.com/articles/s42004-019-0177-5

2018

Maram, L.; Tanaka, F. Mannich reactions of carbohydrate derivatives with ketones to afford polyoxy-functionalized piperidines. Org. Lett. 2019, 21, 1165-1169, doi: 10.1021/acs.orglett.9b00105.
URL: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b00105

Chouthaiwale, P. V.; Aher, R. D.; Tanaka, F.  Catalytic enantioselective formal (4+2) cycloaddition by aldol-aldol annulation of pyruvate derivatives with cyclohexane-1,3-diones to afford functionalized decalins.  Angew. Chem. Int. Ed., 2018, 57, 13298-13301, doi: 10.1002/anie.201808219.  Angew. Chem., 2018, 130, 13482-13485, doi: 10.1002/ange.201808219.
URL: https://doi.org/10.1002/anie.201808219

Enukonda, J.; Johnson, S.; Tanaka, F.  C-Glycosidation of unprotected aldopentoses with ketones using proline-triethylamine as catalyst.  Heterocycles 2018, 99, doi: 10.3987/COM-18-S(F)13.
URL: https://www.heterocycles.jp/newlibrary/libraries/doi
URL (OIST repository): https://oist.repo.nii.ac.jp/records/1100

Zhang, D.; Chuang, P.-S.; Cao, D.; Krishna, Y.; Shilpa, K.; Tanaka, F.  Detection of enantiomers of chiral primary amines by ¹H NMR analysis via enamine formation with an enantiopure γ-position aldol product of a b-keto ester.  Tetrahedron Lett. 2018, 59, 2248-2250, doi: 10.1016/j.tetlet.2018.04.079.
URL: https://www.sciencedirect.com/science/article/pii/S0040403918305653

Johnson, S.; Bagdi, A. K.; Tanaka, F.  C-Glycosidation of unprotected di- and trisaccharide aldopyranoses with ketones using pyrrolidine-boric acid catalysis.  J. Org. Chem. 2018, 83, 4581-4597, doi: 10.1021/acs.joc.8b00340.
URL: https://pubs.acs.org/doi/abs/10.1021%2Facs.joc.8b00340

Chouthaiwale, P. V.; Aher, R. D.; Tanaka, F.  Reactions of pyruvate-derived dihydropyrans with formaldehyde: synthesis of functionalized furopyrans and related products.  Heterocycles 2018, 97, 569-573, doi: 10.3987/COM-18-S(T)29.
URL: https://www.heterocycles.jp/newlibrary/libraries/doi

Yin, F.; Garifullina, A.; Tanaka, F.  Correction: Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones.  Org. Biomol. Chem. 2018, 16, 3052-3053, doi: 10.1039/c8ob90051e.
URL: http://pubs.rsc.org/en/content/articlelanding/2018/ob/c8ob90051e#!divAbstract

2017

Yin, F.; Garifullina, A.; Tanaka, F.  Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones.  Org. Biomol. Chem. 2017, 15, 6089-6092.
URL: http://pubs.rsc.org/en/content/articlelanding/2017/ob/c7ob01484h#!divAbstract

Zhang, D.; Tanaka, F.  Determination of relative frequency of carbanion formation at a-positions of ketones under aldol reaction catalysis conditions.  Org. Lett. 2017, 19, 3803-3806.
URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b01676

Huang, J.-R.; Sohail; M.; Taniguchi, T.; Monde, K.; Tanaka, F.  Formal (4+1) cycloaddition and enantioselective Michael-Henry-cascade reactions to synthesize spiro[4,5]decanes and spirooxindole polycycles.  Angew. Chem. Int. Ed. 2017, 56, 5853-5857.
URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201701049/abstract

Chouthaiwale, P. V.; Lapointe, S.; Tanaka, F.  Synthesis of 4-substituted-pyridine-2,6-dicarboxylic acid derivatives from pyruvates and aldehydes in one pot.  Heterocycles 2017, 95, 587-594.
URL: https://www.heterocycles.jp/newlibrary/downloads/PDF/24781/95/1
URL (OIST repository): https://oist.repo.nii.ac.jp/records/2000417

2016

Kobayashi, K.; Ohshiro, T.; Tomoda, H.; Yin, F.; Cui, H.-L.; Chouthaiwale, P. V.; Tanaka, F.  Discovery of SOAT2 Inhibitors from Synthetic Small Molecules.  Bioorg. Med. Chem. Lett. 2016, 26, 5899-5901.
URL: http://www.sciencedirect.com/science/article/pii/S0960894X16311489

Zhang, D.; Tanaka, F.  Catalytic enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones.  RSC Advances 2016, 6, 61454-61457.
URL: http://pubs.rsc.org/en/content/articlelanding/2016/ra/c6ra13859d#!divAbstract

田中富士枝，酵素と有機分子触媒，CSJ カレントレビュー 22 有機分子触媒の化学，日本化学会編，化学同人 2016年, pp24-29. (In English: Tanaka, F.  Enzymes and organocatalysts, in CSJ Current Review 22 The Chemistry of Organocatalysis, The Chemical Society of Japan, Kagakudojin, 2016, pp24-29.)

Cui, H.-L.; Chouthaiwale, P. V.; Yin, F. ; Tanaka, F.  Catalytic asymmetric hetero-Diels-Alder reactions of enones with isatins to access functionalized spirooxindole tetrahydropyrans: Scope, derivatization, and discovery of bioactives.  Org. Biomol. Chem. 2016, 14, 1777-1783.
URL: http://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02393a#!divAbstract

Johnson, S.; Tanaka, F.  Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones.  Org. Biomol. Chem. 2016, 14, 254-264.
URL: http://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02094h#!divAbstract

Cui, H.-L.; Chouthaiwale, P. V.; Yin, F. ; Tanaka, F.  Reaction-based mechanistic investigations of asymmetric hetero-Diels-Alder reactions of enones with isatins catalyzed by amine-based three-component catalyst systems.  Asian J. Org. Chem. 2016, 5, 153-161.
URL: http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201500412/epdf

2015

Zhang, D.; Tanaka, F.  Aldol reactions of ketone donors with aryl trifluoromethyl ketone acceptors catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for concise access to aryl- and trifluoromethyl-substituted tertiary alcohols.  Adv. Synth. Cat. 2015, 357, 3458-3462.
URL: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500497/abstract

Jithender, E.; Katsuyama, I.; Zhang, D.; Johnson, S.; Tanaka, F.  Aldol reactions of 1,2-diketones catalyzed by amines to afford furanose derivatives. Tetrahedron Lett. 2015, 56, 735-738.
URL: http://www.sciencedirect.com/science/article/pii/S0040403914021716

Tanaka, F.  Development of efficient amine-based catalyst systems: Control of reactions of molecules that act as both nucleophiles and electrophiles. MEXT Grant Advanced Molecular Transformations by Organocatalysts News Letter 2015, No. 39, March 2015.

2014

Chouthaiwale, P. V.; Tanaka, F.  Reactions of pyruvates: organocatalytic synthesis of functionalized dihydropyrans in one pot and further transformations to functionalized carbocycles and heterocycles. Chem. Commun. 2014, 50, 14881-14884.
URL: http://pubs.rsc.org/en/content/articlelanding/2014/cc/c4cc06035k#!divAbstract

Cui, H.-L.; Tanaka, F.  One-pot synthesis of polysubstituted 3-acylpyrroles by cooperative catalysis. Org. Biomol. Chem. 2014, 12, 5822-5826.
URL: http://pubs.rsc.org/en/content/articlelanding/2014/ob/c4ob01019a#!divAbstract

Zhang, D.; Johnson, S.; Cui, H.-L.; Tanaka, F.  Synthesis of furanose spirooxindoles via 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed aldol reactions of a pyruvic aldehyde derivative. Asian J. Org. Chem. 2014, 3, 391-394.
URL: http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201400016/full

Mase, N.; Ando, T.; Shibagaki, F.; Sugita, A.; Narumi, T.; Toda, M.; Watanabe, N.; Tanaka, F.  Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO. Tetrahedron Lett. 2014, 55, 1946-1948.
URL: http://www.sciencedirect.com/science/article/pii/S0040403914002287

Katsuyama, I.; Chouthaiwale, P. V.; Akama, H.; Cui, H.-L.; Tanaka, F.  Fluorogenic probes for aldol reactions: Tuning of fluorescence using p-conjugation systems. Tetrahedron Lett. 2014, 55, 74-78.
URL: http://www.sciencedirect.com/science/article/pii/S0040403913018790

2013

Mase, N.; Takabe, K.; Tanaka, F.  Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence. Tetrahedron Lett. 2013, 54, 4306-4308; erratum 2013, 54, 5140.
URL: http://www.sciencedirect.com/science/article/pii/S0040403913009544

Cui, H.-L.; Tanaka, F.  Catalytic enantioselective formal hetero-Diels-Alder reactions of enones with isatins to give spirooxindole tetrahydropyranones. Chem. Eur. J. 2013, 19, 6213-6216; corrigendum 2013, 19, 12187.
URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201300595/abstract

Katsuyama, I.; Chouthaiwale, P. V.; Cui, H.-L.; Ito, Y.; Sando, A.; Tokiwa, H.; Tanaka, F.  Substituent-dependent reactivity in aldehyde transformations: 4-(phenylethynyl)benzaldehydes versus simple benzaldehydes. Tetrahedron 2013, 69, 4098-4104.
URL: http://www.sciencedirect.com/science/article/pii/S0040402013004316

Tanaka, F.  Synthesis of functionalized molecules and catalyst development strategies. MEXT Grant Advanced Molecular Transformations by Organocatalysts News Letter 2013, No. 21, Sept. 2013.