研究業績
 ORCID orcid.org/0000-0002-0309-9507

論文(責任著者)@新潟大学
45 Full Review
Nitrogen- and Sulfur-Based Stevens and Related Rearrangements
Eiji Tayama
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
44 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
43 Short Review
Recent Advances in the Generation of Onium Ylides for Sommelet-Hauser Rearrangements
Tayama, E.
Synthesis 2022, 54, 5395.

 

DOI: 10.1055/a-1914-7261
42 Research Article
Chiral Tetraalkynylborate as a Chiral Solvating Agent for N-Chiral Tetraalkylammonium Salts
Tayama, E.; Nishio, R.
Tetrahedron 2022, 114, 172783.

 

DOI: 10.1016/j.tet.2022.132783
41 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
40 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 ※オープンアクセス
39 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 ※オープンアクセス
38 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
37 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
36 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
35 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
34 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
33 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
32 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
31 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
30  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
29  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
28 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
27 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
26 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
25 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
24 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
23 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
22  総合論文
第四級アンモニウムイリドを中間体とする塩基促進型Sommelet-Hauser転位の新しい展開
田山 英治
有機合成化学協会誌, 2014, 72, 418-428.

 

DOI: 10.5059/yukigoseikyokaishi.72.418
21 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
20 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
19 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
18  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
新潟大学学術リポジトリ版リポジトリとは?
17 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
新潟大学学術リポジトリ版リポジトリとは?
16 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
新潟大学学術リポジトリ版リポジトリとは?
15 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
新潟大学学術リポジトリ版リポジトリとは?
14  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
13 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
新潟大学学術リポジトリ版リポジトリとは?
12 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
新潟大学学術リポジトリ版リポジトリとは?
11 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
新潟大学学術リポジトリ版リポジトリとは?
10 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
新潟大学学術リポジトリ版リポジトリとは?
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
新潟大学学術リポジトリ版リポジトリとは?
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
新潟大学学術リポジトリ版リポジトリとは?
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
新潟大学学術リポジトリ版リポジトリとは?
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
新潟大学学術リポジトリ版リポジトリとは?
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: 10.1021/ol062042j
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
新潟大学学術リポジトリ版リポジトリとは?
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.

  

DOI: 10.1246/cl.2006.478
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.

   

DOI: 10.1055/s-2006-939053
新潟大学学術リポジトリ版リポジトリとは?
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
新潟大学学術リポジトリ版リポジトリとは?

その他の論文
10 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.
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.
8  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.
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.
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.
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, 54, 6874-6877.
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.
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.
2  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.
1  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.

ポスドク時の発表論文
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.
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. 
Direct Vinylogous Mannich-Type Reactions via Ring Opening and Rearrangement of Vinyloxiranes
Lautens, M.; Tayama, E.; Nguyen, D. 
Org. Lett. 20046, 345-347.

学生時の発表論文
11
Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected α-Amino Acid Amides toward Practical Asymmetric Synthesis of Vicinal Diamines, α-Amino Ketones, and α-Amino Alcohols
Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K. 
J. Am. Chem. Soc. 2005127, 5073-5083.
10
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. 
(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. 
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

受賞等
 2004年 有機合成化学協会研究企画賞(第一製薬)


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