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Dr. Eiji Tayama Home Page
(Last updated 2024.9.20)
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About Eiji Tayama
Eiji Tayama(田山 英治)
Associate Professor of Niigata University
Department of Chemistry
Faculty of Science
Niigata University
E-Mail: tayama[at]chem.sc.niigata-u.ac.jp
Academic Positions
2008-Present Associate Professor, Niigata University
2003-2008 Assistant Professor, Niigata University
Education
2002-2003 Toronto University (CANADA), Post-doctoral fellow with Prof.
Mark Lautens
1997-2002 Hokkaido University, Ph.D. with Prof. Keiji Maruoka
1993-1997 Utsunomiya University, B.Sc.
Areas of Research Interest
The Study of N-Chiral Nitrogen Compounds
Rearrangement Reactions
Elimination reactions
Development of New Synthetic Methods
Synthesis of Unnatural Amino Acid Derivatives
Link
Niigata University
Faculty of Science
Publications
70 |
Research Article
Controlling the position of the
nucleophilic ring-opening of 2-EWG-substituted azetidinium salts with fluoride
by the N-1-(1-naphthyl)ethyl substituent and BINAM-derived bis-urea
organocatalyst
Tayama, E.; Tsutsumi, R.; Uraguchi, D.
Tetrahedron 2024, 167, 134274.

DOI: 10.1016/j.tet.2024.134274 |
69 |
Full Review
Nitrogen- and Sulfur-Based Stevens and Related Rearrangements
Tayama, E.
Comprehensive Organic Synthesis, 3rd Ed., Elsevier.
Pre-released in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

DOI: 10.1016/B978-0-323-96025-0.00029-6 |
68 |
Research Article
Synthesis of α-Fluoro-γ-aminobutyric Acid Derivatives by Nucleophilic Ring-opening
of Azetidine-2-carboxylic Acid-derived Ammonium Salts with Fluoride
Tayama, E.; Kurosaki, Y.; Iida, M.; Aida, T.; Nakanome, N.
Tetrahedron 2023, 142, 133528.

DOI: 10.1016/j.tet.2023.133528 |
67 |
Short Review
Recent Advances in the Generation of Onium Ylides for Sommelet-Hauser Rearrangements
Tayama, E.
Synthesis 2022, 54, 5385.

DOI: 10.1055/a-1914-7261 |
66 |
Research Article
Chiral Tetraalkynylborate as a Chiral Solvating Agent for N-Chiral Tetraalkylammonium Salts
Tayama, E.; Nishio, R.
Tetrahedron 2022, 114, 132783.
DOI: 10.1016/j.tet.2022.132783 |
65 |
Research Article
Base-Induced Sommelet–Hauser Rearrangement of N-(Pyridinylmethyl) Tetraalkylammonium
Salts
Tayama, E.; Shimizu, G.; Nakao R.
Tetrahedron 2022, 111, 132721.

DOI: 10.1016/j.tet.2022.132721 |
64 |
Synthesis of Tertiary Alkyl Fluorides and Chlorides by Site-Selective Nucleophilic
Ring-Opening Reaction of α-Aryl Azetidinium Salts
Tayama, E.; Kawai, K.
RSC Adv. 2021, 11, 39607-39618.

DOI: 10.1039/D1RA08706A ※Open Access |
63 |
Synthesis of Optically Active 2-Substituted Azetidine-2-carbonitriles from Chiral 1-Arylethylamine via α-Alkylation of N-Borane Complexes
Tayama, E.; Nakanome, N.
RSC Adv. 2021, 11, 23825-23837.

DOI: 10.1039/D1RA04585G ※Open Access |
62 |
Brønsted Acid-Catalyzed Aza-Ferrier Reaction of N,O-Allenyl Acetals: Synthesis
of β-Amino-α-methylene Aldehydes
Tayama, E.; Ishikawa, Y.
J. Org. Chem. 2020, 85, 9405-9414.

DOI: 10.1021/acs.joc.0c01047
|
61 |
Base-induced Sommelet-Hauser Rearrangement of N-(α-(2-Oxyethyl)branched)benzylic
Glycine Ester-derived Ammonium Salts via a Chelated Intermediate
Tayama, E.; Hirano, K.; Baba, S.
Tetrahedron 2020, 76, 131064.

DOI: 10.1016/j.tet.2020.131064 |
60 |
Base-promoted Aromatic [3,3] Sigmatropic Rearrangement of N-Acyl-O-arylhydroxylamine
Derivatives
Tayama, E.; Hirano, K.
Tetrahedron 2019, 75, 665-673.

DOI: 10.1016/j.tet.2018.12.058 |
59 |
Chiral Tetraaryl- and Tetraalkynylborates as Chiral Solvating Agents for Tetraalkylammonium Salts
Tayama, E.; Sugawara, T.
Eur. J. Org. Chem. 2019, 803-811.

DOI: 10.1002/ejoc.201801448 |
58 |
Base-promoted Diastereoselective α-Alkylation of Borane N-((S)-1’-Phenylethyl)azetidine-2-carboxylic
acid Ester Complexes
Tayama, E.; Nishio, R.; Kobayashi, Y.
Org. & Biomol. Chem. 2018, 16, 5833-5845.

DOI: 10.1039/C8OB01395K |
57 |
Dearomative [2,3] Sigmatropic Rearrangement of Ammonium Ylides Followed
by 1,4-Elimination to Form α-(ortho-Vinylphenyl)Amino Acid Esters
Tayama, E.; Sotome, S.
Org. & Biomol. Chem. 2018, 16, 4833-4839.

DOI: 10.1039/C8OB01091A |
56 |
Structural and Mechanistic Studies of the Base-Induced Sommelet-Hauser
Rearrangement of N-α-Branched Benzylic Azetidine-2-carboxylic Acid-Derived
Ammonium Salts
Tayama, E.; Watanabe, K.; Sotome, S.
Org. & Biomol. Chem. 2017, 15, 6668-6678.

DOI: 10.1039/C7OB01391D |
55 |
Diaza [1,4] Wittig-Type Rearrangement of N-Allylic-N-Boc-hydrazines into
γ-Amino-N-Boc-Enamines
Tayama, E.; Kobayashi, Y.; Toma, Y.
Chem. Commun. 2016, 52, 10570-10573.

DOI: 10.1039/C6CC04626F |
54 |
Ring-Strain Effect in Base-Induced Sommelet-Hauser Rearrangement: Application
to Successive Stereo-Controlled Transformations
Tayama, E.; Watanabe, K.; Matano, Y.
Eur. J. Org. Chem. 2016, 3631-3641.

DOI: 10.1002/ejoc.201600611 |
53 |
Review
Ring-Substitution, Enlargement, and Contraction by Base-Induced Rearrangements
of N-Heterocyclic Ammonium Salts Tayama, E.
Heterocycles 2016, 92, 793-828.

DOI: 10.3987/REV-16-837 |
52 |
Solvent-Dependent Reaction Pathways Operating in Copper(II) Tetrafluoroborate
Promoted Oxidative Ring-Opening Reactions of Cyclopropyl Silyl Ethers
Hasegawa, E.; Nemoto, K.; Nagumo, R.; Tayama, E.; Iwamoto, H.
J. Org. Chem. 2016, 81, 2692-2703. |
51 |
Regioselective Synthesis of Secondary 1,3-Dienamides by Successive Eliminations
Tayama, E.; Saito, S.
Tetrahedron 2016, 72, 599-604.

DOI: 10.1016/j.tet.2015.11.065
|
50 |
Synthesis of Linear [5]Catenanes via Olefin Metathesis Dimerization of Pseudorotaxanes Composed of a [2]Catenane and a Secondary Ammonium Salt
Iwamoto, H.; Tafuku, S.i; Sato, Y.; Takizawa, W.; Katagiri, W.; Tayama,
E.; Hasegawa, E.; Fukazawa, Y.; Haino, T.
Chem. Commun. 2016, 52, 319-322. |
49 |
Personal Account
Recent Advances in the Base-Induced Sommelet-Hauser Rearrangement of Amino
Acid-Derived Ammonium Ylides
Tayama, E.
Chem. Rec. 2015, 789-800.

DOI: 10.1002/tcr.201500009 |
48 |
Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation
of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-Butadienyl Derivatives
Tayama, E.; Saito, S.
Synlett 2015, 1880-1884.

DOI: 10.1055/s-0034-1380426 |
47 |
Aryl-Substituted Dimethylbenzimidazolines as Effective Reductants of Photoinduced
Electron Transfer Reactions
Hasegawa, E.; Ohta, T.; Tsuji, S.; Mori, K.; Uchida, K.; Miura, T.; Ikoma,
T.; Tayama, E.; Iwamoto, H.; Takizawa, S.; Murata, S.
Tetrahedron 2015, 71, 5494-5505. |
46 |
|
45 |
Stereoselective Preparation of (1Z)- and (1E)-N-Boc-1-Amino-1,3-Dienes
by Stereospecific Base-Promoted 1,4-Elimination
Tayama, E.; Toma, Y.
Tetrahedron 2015, 71, 554-559.

DOI: 10.1016/j.tet.2014.12.039 |
44 |
Double Axial Chirality Promoted Asymmetric [2,3] Stevens Rearrangement
of N-Cinnamyl L-Alanine Amide-Derived Ammonium Ylides
Tayama, E.; Naganuma, N.; Iwamoto, H.; Hasegawa, E.
Chem. Commun. 2014, 50, 6860-6862.

DOI: 10.1039/C4CC02536A |
43 |
Copper(II)-Acid Catalyzed Cyclopropanation of 1,3-Dienamides by Electrophilic
Activation of α-Aryl Diazoesters
Tayama, E.; Horikawa, K.; Iwamoto, H.; Hasegawa, E.
Tetrahedron Lett. 2014, 55, 3041-3044.

DOI: 10.1016/j.tetlet.2014.03.115 |
42 |
Personal Account
New Development of Base-Induced Sommele-Hauser Rearrangement of Ammonium
Ylides
Tayama, E.
J. Synth. Org. Chem., Japan, 2014, 72, 418-428.

DOI: 10.5059/yukigoseikyokaishi.72.418 |
41 |
A Photo-Reagent System of Benzimidazoline and Ru(bpy)3Cl2 to Promote Hexenyl Radical Cyclization and Dowd-Beckwith Ring-Expansion
of α-Halomethyl-Substituted Benzocyclic 1-Alkanones
Hasegawa, E.; Tateyama, M.; Hoshi, T.; Ohta, T.; Tayama, E.; Iwamoto, H.;
Takizawa, S.; Murata, S.
Tetrahedron 2014, 70, 2776-2783. |
40 |
Carbon-Carbon Bond Formation via Benzoyl Umpolung Attained by Photoinduced
Electron-Transfer with Benzimidazolines Igarashi, T.; Tayama, E.; Iwamoto, H.; Hasegawa, E.
Tetrahedron Lett. 2013, 52, 1819-1821. |
39 |
Copper(II)-Salt-Promoted Oxidative Ring-Opening Reactions of Bicyclic Cyclopropanol
Derivatives via Radical Pathways
Hasegawa E.; Tateyama, M.; Nagumo, R.; Tayama E.; Iwamoto, H.
Beilstein J. Org. Chem. 2013, 9, 1397-1406. |
38 |
Selective Synthesis of [2]- and [3] Catenane Tuned by Ring Size and Concentration
Iwamoto, H.; Takizawa, W.; Itoh, K.; Hagiwara, T.; Tayama, E.; Hasegawa, E.; Haino T.
J. Org. Chem. 2013, 78, 5205-5217. |
37 |
1,4-Elimination/Bronsted Acid Catalyzed Aza-Ferrier Reaction Sequence as
an Entry to β-Amino-β,γ-Unsaturated Aldehydes
Tayama, E.; Horikawa, K.; Iwamoto, H.; Hasegawa, E.
Tetrahedron 2013, 69, 2745-2752.

DOI: 10.1016/j.tet.2013.01.088
|
36 |
A Unique and Simple Preparative Method for α-Arylpipecolinic Acid Esters
via Base-induced Sommelet-Hauser Rearrangement
Tayama, E.; Sato, R.; Ito, M.; Iwamoto, H.; Hasegawa, E.
Heterocycles 2013, 87, 381-388.

DOI: 10.3987/COM-12-12619 |
35 |
An Effective Procedure to Promote Aza-Prins Cyclization Reactions Employing
a Combination of Ferric Chloride and an Imidazolium Salt in Benzotrifluoride
Osawa, C.; Tateyama, M.; Miura, K.; Tayama, E.; Iwamoto, H.; Hasegawa, E.
Heterocycles 2012, 86, 1211-1226.
DOI: 10.3987/COM-12-S(N)78 |
34 |
Copper(II)-Acid Co-Catalyzed Intermolecular Substitution of Electron-Rich
Aromatics with Diazoesters Tayama, E.; Ishikawa, M.; Iwamoto, H.; Hasegawa,
E. Tetrahedron Lett. 2012, 53, 5159-5161.

DOI:
10.1016/j.tetlet.2012.07.070 |
33 |
A Formal Method for the De-N,N-Dialkylation of Sommelet-Hauser Rearrangement
Products
Tayama, E.; Sato, R.; Takedachi, K.; Iwamoto, H.; Hasegawa, E.
Tetrahedron 2012, 68, 4710-4718.

DOI: 10.1016/j.tet.2012.04.015
|
32 |
1,2-Dimethoxy-4,5-dimethylene: A New Protecting Group for Acyclic Amino Acid Derivatives Prepared by Stevens Rearrangement Tayama, E.; Takedachi, K.; Iwamoto, H.; Hasegawa, E.
Tetrahedron Lett. 2012, 53, 1373-1375.

DOI: 10.1016/j.tetlet.2012.01.013 |
31 |
Asymmetric α-2-Tosylethenylation of N,N-Dialkyl-L-Amino Acid Esters via the Formation of Non-Racemic Ammonium Enolates
Tayama, E.; Igarashi, T.; Iwamoto, H.; Hasegawa, E.
Org. Biomol. Chem. 2012, 10, 339-345.

DOI: 10.1039/C1OB06074K |
30 |
Asymmetric α-2-Tosylvinylation of in situ-generated N-2-Tosylvinyl Proline-Derived Ammonium Ylides
Igarashi, T.; Tayama, E.; Iwamoto, H.; Hasegawa, E.
Tetrahedron Lett. 2011, 52, 1819-1821.
DOI: 10.1016/j.tetlet.2011.02.040 |
29 |
Copper(II) Triflate Catalyzed Intermolecular Aromatic Substitution of N,N-Disubstituted
Anilines with Diazoesters
Tayama, E.; Yanaki, T.; Iwamoto, H.; Hasegawa, E.
Eur. J. Org. Chem. 2010, 6719-6721.

DOI: 10.1002/ejoc.201001083 |
28 |
Application of Biphasic Reaction Procedure using Ferric Chloride Dissolved in An Imidazolium Salt and Benzotrifluoride (FeIm-BTF Procedure) to Aza-Prins Cyclization Reaction
Hasegawa, E.; Hiroi, N.; Osawa, C.; Tayama, E.; Iwamoto, H.
Tetrahedron Lett. 2010, 51, 6535-6538. |
27 |
Remarkable Enhancement Effect of Potassium tert-Butoxide/THF Solution in
Base-induced Sommelet-Hauser Rearrangements
Tayama, E.; Takedachi, K.; Iwamoto, H.; Hasegawa, E.
Tetrahedron 2010, 66, 9389-9395.

DOI: 10.1016/j.tet.2010.09.105 |
26 |
Resolution of Nitrogen-Centered Chiral Tetraalkylammonium Salts: Application
to [1,2] Stevens Rearrangements with N-to-C Chirality Transmission
Tayama, E.; Otoyama, S.; Tanaka, H.
Tetrahedron: Asymmetry 2009, 20, 2600-2608.

DOI: 10.1016/j.tetasy.2009.10.025 |
25 |
New Synthetic Routes to Optically Active α-Quaternary α-Aryl Amino Acid Derivatives via the Diastereoselective Stevens and Sommelet-Hauser Rearrangements
Tayama, E.; Orihara, K.; Kimura, H.
Org. & Biomol. Chem. 2008, 6, 3673-3680.

DOI: 10.1039/b811162f |
24 |
Bronsted Acid Catalyzed Regioselective Aza-Ferrier Reaction: A Novel Synthetic Method of
α-(N-Boc-2-pyrrolidinyl)aldehydes
Tayama, E.; Otoyama, S.; Isaka W.
Chem. Comm. 2008, 4216-4218.
DOI: 10.1039/b806492j |
23 |
Asymmetric Sommelet-Hauser Rearrangement of N-Benzylic Ammonium Salts
Tayama, E.; Kimura, H.
Angew. Chem. Int. Ed. 2007, 46, 8869-8871.

DOI: 10.1002/anie.200703832 |
22 |
A Facile Synthetic Method of α-Quaternary-β,γ-Unsaturated Aldehydes via the Stereoselective 1,4-Elimination and α-Regioselective Ferrier Reaction
Tayama, E.; Hashimoto, R.
Tetrahedron Lett. 2007, 48, 7950-7952.
DOI: 10.1016/j.tetlet.2007.09.049 |
21 |
A Facile Method for the Stereoselective Preparation of (1E,3E)-4-Substituted-1-Amino-1,3-Dienes
via 1,4-Elimination
Tayama, E.; Sugai, S.
Tetrahedron Lett. 2007, 48, 6163-6166.
DOI: 10.1016/j.tetlet.2007.06.140 |
20 |
An Efficient Optical Resolution of Nitrogen-Centered Chiral β-Hydroxy-Tetraalkylammonium
Salts via Complexation with (R)-BINOL
Tayama, E.; Tanaka, H.
Tetrahedron Lett. 2007, 48, 4183-4185.

DOI: 10.1016/j.tetlet.2007.04.078 |
19 |
Regio- and Stereoselective Ferrier Reaction of O-1,3-Dienyl Acetals
Promoted by Organoaluminum Complexes
Tayama, E.; Isaka, W.
Org. Lett. 2006, 8, 5437-5439.

DOI: 10.1016/j.tetlet.2007.04.078 |
18 |
A Facile and Stereoselective Synthetic Method for Allylic 1,3-Dienyl Ethers
Tayama, E.; Sugai, S.; Hara, M.
Tetrahedron Lett. 2006, 47, 7533-7535.
DOI: 10.1016/j.tetlet.2006.08.100 |
17 |
Asymmetric [1,2] Stevens Rearrangement of (S)-N-Benzylic Proline-Derived
Ammonium Salts under Biphasic Conditions
Tayama, E.; Nanbara, S.; Nakai, T.
Chem. Lett. 2006, 35, 478-479.
|
16 |
A Facile Method for the Stereoselective Preparation of (1Z,3E)-Dienyl Ethers
via 1,4-Elimination of 1,4-Dialkoxy-(2Z)-alkenes with n-Butyllithium
Tayama, E.; Sugai, S.
Synlett 2006, 849-852.
|
15 |
Kinetic Resolution via the [2,3] Stevens Rearrangement of Epimeric Six-Membered
Ammonium Ylides: A New Entry to Enantio-Enriched α-Amino Acid Derivatives
Tayama, E.; Tanaka, H.; Nakai, T.
Heterocycles 2005, 66, 95-99.
DOI: 10.3987/COM-05-S(K)39 |
14 |
Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected α-Amino
Acid Amides toward Practical Asymmetric Synthesis of Vicinal Diamines, α-Amino
Ketones, and a-Amino Alcohols
Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K.
J. Am. Chem. Soc. 2005, 127, 5073-5083.
|
13 |
Palladium-Catalyzed Intramolecular Coupling between Aryl Iodides and Allyl Moieties via Thermal and Microwave-Assisted Conditions
Lautens, M.; Tayama, E.; Herse, C.
J. Am. Chem. Soc. 2005, 127, 72-73.
|
12 |
Activation and Stabilization of Aldimines by an ortho-Trifluoromethyl
Substituent in Direct Vinylogous Mannich-type Reactions
Lautens, M.; Tayama, E.; Nguyen, D.
Tetrahedron Lett. 2004, 45, 5131-5133.
|
11 |
Stereoselective Terminal Functionalization of Small Peptides for Catalytic Asymmetric Synthesis of Unnatural Peptides
Maruoka, K.; Tayama, E.; Ooi, T.
Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5824-5829.
|
10 |
(2,7-Disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) as Bidentate
Organoaluminum Lewis Acids: Elucidation and Synthetic Utility of the
Double Electrophilic Activation Phenomenon
Ooi, T.; Takahashi, M.; Yamada, M.; Tayama, E.; Omoto, K.; Maruoka, K.
J. Am. Chem. Soc. 2004, 126, 1150-1160.
|
9 |
Direct Vinylogous Mannich-Type Reactions via Ring Opening and Rearrangement
of Vinyloxiranes
Lautens, M.; Tayama, E.; Nguyen, D.
Org. Lett. 2004, 6, 345-347.
|
8 |
Practical Asymmetric Synthesis of Vicinal Diamines throgh the Catalytic
Highly Enantioselective Alkylation of Glycine Amide Derivatives
Ooi, T.; Sakai, D.; Takeuchi, M.; Tayama, E.; Maruoka, K.
Angew. Chem. Int. Ed. 2003, 42, 5868-5870.
|
7 |
Highly Stereoselective N-Terminal Functionalization of Small Peptides by Chiral Phase-Transfer Catalysis
Ooi, T.; Tayama, E.; Maruoka, K.
Angew. Chem. Int. Ed. 2003, 42, 579-582. |
6 |
Activation of Ether Functionality of Allyl Vinyl Ethers by Chiral Bis(organoaluminum) Lewis Acids: Application to Asymmetric Claisen Rearrangement
Tayama, E.; Saito, A.; Ooi, T.; Maruoka, K.
Tetrahedron 2002, 58, 8307-8312. |
5 |
Remarkable Template Effect of a Lewis Acid Receptor in the Intramolecular Radical Cyclization: Control of Reaction Pathway as well as Stereochemistry
Ooi, T.; Hokke, Y.; Tayama, E.; Maruoka, K.
Tetrahedron 2001, 57, 135-144. |
4 |
Dramatic Rate Enhancement by Ultrasonic Irradiation in Liquid-Liquid Phase-Transfer Catalytic Reactions
Ooi, T.; Tayama, E.; Doda, K.; Takeuchi, M.; Maruoka, K.
Synlett 2000, 1500-1502. |
3 |
Dramatic Enhancement of Reactivity of Organosilicon Compounds Induced by Complexation of Bis(allyl)silanes with Fluoride Ion
Shibato, A.; Itagaki, Y.; Tayama, E.; Hokke, Y.; Asao, N.; Maruoka, K.
Tetrahedron 2000, 56, 5373-5382. |
2 |
Efficient Synthesis of Aromatic sec-Amides from Esters: Synthetic Utility of Dilithium
Amides
Ooi, T.; Tayama, E.; Yamada, M.; Maruoka, K.
Synlett 1999, 729-730. |
1 |
Bidentate organoaluminum Lewis acid for selective activation of carbonyl over acetal functionality: Chemoselective functionalization
Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K.
Tetrahedron Lett. 1997, 38, 7403-7406 |
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