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Researcher Information

last modified:2017/05/23

Professor SEGI Masahito

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Faculty, Affiliation

Faculty of Chemistry, Institute of Science and Engineering

College and School Educational Field

Division of Material Chemistry, Graduate School of Natural Science and Technology
Division of Material Sciences, Graduate School of Natural Science and Technology
School of Chemistry, College of Science and Engineering

Laboratory

 TEL:076-234-4787 FAX:076-234-4800

Academic Background

【Academic background(Doctoral/Master's Degree)】
Kanazawa University Master 198003 Completed
【Academic background(Bachelor's Degree)】
Kanazawa University 197803
【Degree】
Doctor of Engineering

Career

Kanazawa University(1980/04/01-1990)
Kanazawa University(1990/04/01-1996/01/31)
Kanazawa University(1996/02/01-2007/05/31)
Kanazawa University(2007/06/01-)
Kanazawa University(2008/04/01-)

Year & Month of Birth

1956/03

Academic Society

The Chemical Society of Japan
The Society of Synthetic Organic Chemistry, Japan
The Kinki Chemical Society, Japan
American Chemical Society

Award

American Chemical Society
American Chemical Society
○ICHAC-3 Poster Prize(1992/06/11)

Specialities

Synthetic organic chemistry、Heterocyclic Chemistry、Organic Reaction、Synthetic chemistry、Organic chemistry、Functional solid state chemistry

Speciality Keywords

Synthetic Chemistry Heteroatom Chemistry Organic Chemistry

Research Themes

Synthesis and Reaction of Highly Reactive Compounds Involving Chalcogen Multiple

Multiple bonded compounds containing heteroatoms lower than the third periodic law are extremely unstable, so it is often said that the reaction control of them are difficult, conversely, they are higly reactive and are expected to be excellent intermediates in organic reactions. In our laboratory, new reagents have been developed, that are enable to use in conversion of oxygen atom of carbonyl compounds to other calcogen atoms (S, Se, Te) directly to form C=S, C=Se, and C=Te compounds. Moreover, these products show high dienophilic character toward cycloaddition reactions with conjugated dienes, heterodienes, and 1,3-dipoles to give new heterocyclic compounds and biomaterials.

Synthesis of Asymmetric Bidentate Ligands Involving Sulfur or Selenium Atoms

In the field of medicinal chemistry, asymmetric synthesis of organic compounds catalyzed by organometallic complexes are very important. So far many kinds of asymmetric ligands have been developed and high enantiomeric excesses have been obtaind. But asymmetric ligands having calcogen atoms such as sulfur and selenium are less known although many unexpected feature may be still remained. In this research, synthesis of bidentate ligands having sulfur and selenium from optically active lactones are continuing.

Development of New Synthetic Methods Based on Organometallic and Organoheteroatom Chemistry

Transformation of functional groups using characteristics of various elements in periodic table is more and more required in recent organic chemistry. We are studying about sequential reactions using transition metals such as Zr, Ti, Cu, Zn, Pd, and heteroatoms such as S, Se, and Te, with the aim to develop new synthetic reactions to give highly functionalized compounds from readily available starting materials. So far fields of organometallic chemistry and heteroatom chemistry exist independently, but we would like to connect these two fields, expecting open a new multiple field.

Books

  •  Science of Synthesis, Vol. 39: Compounds with One Saturated Carbon-Heteroatom Bond: Sulfur, Selenium, and tellurium Thieme 2007/11

Papers

  •  [4+2] Dimerization and Cycloaddition Reaction of a,b-Unsaturated Selenoaldehydes and Selenoketones JOURNAL OF ORGANIC CHEMISTRY 64 5 1565-1575 1999/03
  •  On the Behavior of a,b-Unsaturated Thioaldehydes and Thioketones in the Diels-Alder Reaction JOURNAL OF ORGANIC CHEMISTRY 65 20 6601-6612 2000/10
  •  Reaction of Selenocarbonyl Compounds with Oxygen-functionalized Conjugated Dienes Phosphorus, Sulfur Silicon Related Elements 136,137&138 12 599-602 1998/12
  •  Reversal of p-Facial Diastereoselection in the Hydride Reduction of Selenanones. Further Application of the Exterior Frontier Orbital Extension Model TETRAHEDRON LETTERS 41 23 4597-4601 2000/06
  •  Synthesis and Structure of Telluroamides and Selenoamides. The First Crystallographic Study of Telluroamides ORGANOMETALLICS 16 4 756-762 1997/04

show all

  •  [3+2] Cycloaddition between Nitrile Oxides or Nitrile Imines and Selenoaldehydes Generated by Retro Diels-Alder Reaction Proceeding of 2000 International Chemical Congress of Pacific Basin Societies 1606 2000/12
  •  [3+2] Cycloaddition Reaction of Selenoaldehydes with 1,3-Dipoles Proceeding of the 5th International Conference on Heteroatom Chemistry 83 1998/07
  •  [4+2] Dimerization and Cycloaddition Reactions of a,b-Unsaturated Selenoaldehydes, Selenoketones, Thioaldehydes, and Thioketones Proceeding of the 5th International Conference on Heteroatom Chemistry 28 1998/07
  •  Acid-catalyzed Rearrangement of Cyclopropylacylsilanes and Cyclopropylsilylcarbinols Proceeding of the 7th International Kyoto Conference on New Aspects of Organic Chemistry 177 1997/11
  •  Generation and Reaction of Reactive Molecules Involving Phosphorus-Chalcogen Double Bonds Proceeding of the 6th International Conference on Heteroatom Chemistry 175 2001/06
  •  Olefination of Carbonyl Compounds with an Arylselenenyl Group by Organotitanium Reagents Followed by Functionalization via Deselenation Proceeding of the 44th Symposium on Organometallic Chemistry 220-221 1997/09
  •  Reaction of Vinylic Organocuprates Formed via Sequential Hydrozirconation-Transmetalation of 1-Alkynes Having a Phenylseleno Group with Electrophiles Proceeding of the 5th International Symposium on Carbanion Chemistry 149 1998/08
  •  Stereochemistry of Nucleophilic Addition Reaction to b-Alkoxyacylsilanes Proceeding of the 48th Symposium on Organometallic Chemistry 404-405 2001/09
  •  Synthesis of Polyfunctionalized Compounds Utilizing Hydrozirconation of 1-Alkynes Having a Phenylseleno Group Proceeding of 2000 International Chemical Congress of Pacific Basin Societies 797 2000/12
  •  Diastereoselective Aldol Condensation of Acylsilane Silyl Enol Ethers with Acetals TETRAHEDRON 58 34 6815-6823 2002/09
  •  The Reaction of Selenoaldehydes with 2-Methoxyfuran Using Their Generation by Retro Diels-Alder Reaction TETRAHEDRON LETTERS 44 6 1179-1182 2003/02
  •  Generation of Selenoaldehydes via Retro Diels-Alder Reaction and the Cycloaddition with Enophiles JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 61 7 661-669 2003/07
  •  Generation of Selenoaldehydes via Retro Diels-Alder Reaction and Their Behavior in the Reaction with Some Enophiles PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS 180 3 & 4 1045-1049 2005/03
  •  Stereoselective Tandem Aldol-Tishchenko Reaction with Acylsilanes CHEMISTRY LETTERS 34 4 466-467 2005/04
  •  Stereoselective Acid-catalyzed Homoallylic Rearrangement of Cyclopropylsilylmethanols: An Efficient Route to Z-Homoallyl Derivatives TETRAHEDRON LETTERS 46 38 6465-6468 2005/09
  •  An Efficient Synthesis of 5-Silyl-2,3-dihydrofurans via Acid-catalyzed Ring-enlargement of Cyclopropyl Silyl Ketones and Their Functionalization TETRAHEDRON LETTERS 46 43 7345-7348 2005/11
  •  Stereoselective Construction of 1,3-Diol Derivatives via Nucleophilic Reaction to b-Methoxysilanes CHEMISTRY LETTERS 34 10 1432-1433 2005/10
  •  Acid-Catalyzed Reaction Behavior of 1-Silylcyclopropylmethanols 47 32 5751-5754 2006/08
  •  An Efficient 1,3-Dipolar Cycloaddition between Aromatic Selenoaldehydes and Nitrile Oxides or Nitrile Imines: An Easy Access to Selenium-Containing Five-Membered Heterocyclic Ring System 48 13 2303-2306 2007/03
  •  Stereoselective Hetero Diels-Alder Reaction of Selenoaldehydes with Pentavalent Phosphole Chalcogenides 48 19 3349-3354 2007/05
  •  Reaction Behavior of Cyclopropylmethyl Cations Derived 1-Phenylselenocyclopropylmethanols with Acids 65 45  9403-9411 2009/11
  •  Acid-catalyzed Reaction Behavior of 1-Phenylselenocyclopropylmethanols M. Honda, T. Nishizawa, Y. Nishii. M. Segi CHEMISTRY LETTERS 37 9 946-947 2008/09
  •  [3+2] Cycloaddition of Seleno- and Thioaldehydes with Cyclic Azomethine Imines HETEROCYCLES 84 1 393-400 2012/01
  •  The Reaction of 1-Silylcyclopropyl Anions with Dichloromethyl Methyl Ether: The Efficient Synthesis of Cyclopropyl Silyl Ketones via Cyclopropylidene Derivatives 51 9, 1294-1297 2010/03
  •  A Stereoselective Approach to (Z)-1-Silyl-2-aryl-1,3-dienes from 4-(Phenylseleno)but-1-yne via Palladium-catalyzed Silylstannylation and Selenoxide Elimination SYNTHESIS-STUTTGART 45 3 341-346 2013/02
  •  An efficient synthesis of cyclopropyl silyl ketones TETRAHEDRON 67 49 9500-9508 2011/12
  •  Conjugate Addition of Vinylic Organocuprates Generated via Transmetalation of Phenylseleno-Substituted Vinylzirconates. Functionalization at the 4-Position of Enones  22 3-4 545-552 2011/08
  •  Reaction of acylsilanes with α-sulfinyl carbanions: regioselective synthesis of silyl enol ethers TETRAHEDRON LETTERS 52 29 3740-3742 2011/07
  •  Synthesis of Selenohydantoins from Isoselenocyanates and alfa-Amino Acids 82 2 1709-1717 2011/01
  •  One-pot synthesis of selenoureas and selenocarbamates via selenation of isocyanates with bis(dimethylaluminum) selenide TETRAHEDRON LETTERS 52 3 415-417 2011/01
  •  Synthetic transformation of homopropargylic selenides to conjugated diene-substituted alcohols and amines using diisopropoxy(η2-alkyne)titanium intermediates TETRAHEDRON 69 21 4311-4324 2013/05
  •  Synthesis and fluorescence properties of dioxa-, dithia-, and diselena-[3.3](1,3)pyrenophanes Maeda, H., Hironishi, M., Ishibashi, R., Mizuno, K., Segi, M. Photochemical & Photobiological Sciences 16 2 228-237 2017/02
  •  Stereoselective Synthesis of Allyl Ethers Using α,β-Unsaturated Acylsilanes Honda, M., Takatera, T., Ui, R.; Kunimoto, K.-K., Segi, M. Tetrahedron Letters 58 9 864-869 2017/03
  •  Magnesium‐Alkoxide Directed Photoaddition of Tetrahydrofurans to γ,γ-Disubstituted Allylic Alcohols Watanabe, Y., Sakai, T., Maeda, H., Segi, M., Soeta, T., Ukaji, Y Heterocycles 93 2 833-844 2016/12

Conference Presentations

  • Synthesis, Fluorescence, and Photoreactions of Stilbene Derivatives Containing Silyl Groups(conference:26th IUPAC International Symposium on Photochemistry)(2016/04)
  • Novel Synthetic Approach to 4'-Selenonucleoside Derivatives via Cycloaddition of Selenoaldehydes Followed by Stereospecific Ring Contraction(conference:13th International Conference on the Chemistry of Selenium and Tellurium)(2016/05)

Arts and Fieldwork

Patent

Theme to the desired joint research

○Joint Research on Synthesis of Heterocyclic Compounds Involving Chalcogen Atoms

Grant-in-Aid for Scientific Research

○「4族遷移金属錯体による炭素結合形成を利用する効率的分子変換反応の開発」(1997-) 
○「有機ジルコニウム化合物およびセレン元素の特性を活用した効率的官能基導入法の開発」(1997-) 
○「遷移金属錯体による炭素結合形成を利用する効率的官能基変換反応の開発」(1998-) 
○「有機ジルコニウム化合物およびセレン元素の特性を活用した効率的官能基導入法の開発」(1998-) 
○「遷移金属錯体による炭素結合形成を利用する効率的官能基変換反応の開発」(1999-) 
○「複数の元素の協同作用を利用する多官能性分子構築法の開発」(1999-) 
○「複数の元素の協同作用を利用する多官能性分子構築法の開発」(2000-) 
○「炭素三員環とシリル基の特性を利用した立体選択的合成反応の開発」(2001-) 

Classes (Bachelors)

○World of Chemistry(2017)
○Laboratory Course IV(2017)
○Exercise I in Applied Chemistry(2017)
○Organic Reaction Mechanisms(2017)
○Laboratory Course IV(2017)
○Organic Chemistry I(2017)
○World of Chemistry(2017)
○Organic Chemistry I(2016)
○Organic Reaction Mechanisms(2016)
○Exercise I in Applied Chemistry(2016)
○Laboratory Course IV(2016)
○Fundamentals of Organic Chemistry(2016)
○Laboratory Course IV(2016)
○World of Chemistry(2016)

Classes (Graduate Schools)

○Introduction of Material Program(2017)
○Organic Main Group Element Chemistry(2017)
○Organic Main Group Element Chemistry(2017)
○Organic Main Group Element Chemistry(2017)
○Organic Main Group Element Chemistry(2017)
○Synthetic Chemistry of Organic Materials(2017)
○Organic Functional Chemistry(2017)
○Synthetic Chemistry of Organic Materials(2016)
○Introduction of Material Program(2016)
○Organic Main Group Element Chemistry(2016)
○Organic Functional Chemistry(2016)

International Project

International Students

Lecture themes

Others (Social Activities)

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