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Dr. Eiji Tayama Home Page
(Last updated 2024.9.20)

I will not respond to emails with the following contents (1 and 2).

1. Our group is not able to employ postdoctoral applicants at this time.

2. I do not accept any international student without introduction from a
researcher close to me or a grant (e.g., JICA).

Because our research funding are limited. There is no research funding
for many students. “MEXT" is not a grant for our laboratory.
In addition, no laboratory space because of many students. The number
of foreign students is limited to 1 person (1 person currently enrolled).


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
Metal-Free, One-Pot, Sequential Protocol for Transforming α,β-Epoxy Ketones to β-Hydroxy Ketones and α-Methylene Ketones
Hasegawa, E.; Arai, S.; Tayama, E.; Iwamoto, H.
J. Org. Chem.
2015, 80, 1593-1600.
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 200920, 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.
20086, 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. 200746, 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. 200748, 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. 200748, 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. 200748, 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. 20068, 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. 200647, 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. 200635, 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 200566, 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. 2005127, 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. 2005127, 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. 200445, 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. 2004101, 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. 2004126, 1150-1160. 
Direct Vinylogous Mannich-Type Reactions via Ring Opening and Rearrangement of Vinyloxiranes
Lautens, M.; Tayama, E.; Nguyen, D. 
Org. Lett. 20046, 345-347.
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. 200342, 5868-5870. 
Highly Stereoselective N-Terminal Functionalization of Small Peptides by Chiral Phase-Transfer Catalysis
Ooi, T.; Tayama, E.; Maruoka, K.
Angew. Chem. Int. Ed. 200342, 579-582.
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 200258, 8307-8312.
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 200157, 135-144.
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. 
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 200056, 5373-5382.
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.
Bidentate organoaluminum Lewis acid for selective activation of carbonyl over acetal functionality: Chemoselective functionalization 
Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K.
Tetrahedron Lett. 199738, 7403-7406