Barluenga Lecture

 
Prof. Dr. Hisashi Yamamoto  
Barluenga Lecture

 

  Speaker





 

 

Prof. Dr. Hisashi Yamamoto

Chubu University
Chicago University, Professor Emeritus
Chicago University, The Yamamoto Group

2018 Fifth Barluenga Conference

 

Education | Research and professional experience | Research Interests | Selected papers | Awards
     

Education

 

1971 Ph.D. Organic Chemistry, Harvard University
1967 BS Organic Chemistry, Kyoto University

     

Research and professional experience



 

1971-1972 Researcher, Toray Industries, Inc. (Prof. J. Tsuji, Adviser)
1972-1976 Instructor, Kyoto University
1976-1977 Lecturer, Kyoto University
1977-1980 Associate Professor, University of Hawaii
1980-1983 Associate Professor, Nagoya University
1983-2002 Professor, Nagoya University 2003 Professor Emeritus, Nagoya University
2002- Professor, The University of Chicago
2012- Professor Emeritus, University of Chicago
2012- Professor and Director of Molecular Catalyst Research Center, Chubu University
2012- Research Supervisor, JST Crest Project of Molecular Technology

   

^

Research Interests

 
 

Due in large part to the development of new reagents, chemists today have the ability to routinely carry out syntheses which would have been impossible to carry out a few decades ago. Proton plays an important role in most enzymatic reactions. A well designed acid catalysis is an excellent candidate, as a proton substitute, for man-made organic reactions. The goal of our research is to engineer an artificial proton of a special shape that can be utilized as an effective tool for chemical reactions by harnessing the high reactivity of the metal atom towards a variety of functional groups. This concept was initially researched by examining the influence of a specially designed organometallic reagent on various organic reactions. The successful discrimination observed lead to examine a more intricate question of enantioface differentiation, which was initially reported from our laboratory and is now widely expanded in the world. During the last decade the uninterrupted expansion of Lewis and Brønsted acid catalysis research has continued in organic synthesis. New catalysis research in our laboratory is targeting more versatile, more selective, and more reactive catalysts, aiming at environmentally benign systems. Nonetheless, the full potential of acid catalysts is still not yet realized. The following topics are recently being studied in our laboratories: 

1. Combined acid catalysis of Lewis and Brønsted acids. 
2. Asymmetric transformation of esterification, amidation, halogenation using designer acid catalysis. 
3. Development of catalytic asymmetric reactions using optically active silver complexes. 
4. Catalytic asymmetric oxidation using metal and non-metal catalyst. 
5. Super Sily for one-pot and/or flow organic synthesis. 
6. Super Brønsted Acid catalysis. 
7. New metal catalysis using cis-Β-configuration.

   

^

Selected papers  

[26] Chiral Phosphoric Acid-Catalyzed Kinetic Resolution via Amide Bond Formation, Shimoda, Y.; Yamamoto, H. J. Am. Chem. Soc. 139, 6855-6858 (2017)

[25] Catalytic Asymmetric Bromocyclization of Polyenes, Samanta, R. C.; Yamamoto, H. J. Am. Chem. Soc. 139, 1460-1463 (2017)

[24] Hydroxy-Directed Amidation of Carboxylic Acid Esters Using a Tantalum Alkoxide Catalyst, Tsuji, H.; Yamamoto, H. J. Am. Chem. Soc. 138, 14218-14221 (2016)

[23] Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides, Bhadra, S.; Yamamoto, H. Angew. Chem. Int. Ed. 55, 13043-13046 (2016)

[22] A Powerful Chiral Phosphoric Acid Catalyst for Enantioselective Mukaiyama–Mannich Reactions, Zhou, F.; Yamamoto, H. Angew. Chem. Int. Ed. 55, 8970-8974 (2016)

[21] Design of a New Bimetallic Catalyst for Asymmtric Epoxidation and Sulfoxidation, Bhadra, S., Akakura, M.; Yamamoto, H., J. Am. Chem. Soc., 137, 15612-15615. (2015)

[20] Catalytic Enantioselective Nitroso Diels-Alder Reaction, Maji, B.; Yamamoto, H., J. Am. Chem. Soc., 137, 15957-15963 (2015).

[19] Gadolinium-​Catalyzed Regio- and Enantioselective Aminolysis of Aromatic trans-​2,​3-​Epoxy Sulfonamides, Wang, C.; Yamamoto, H., Angew. Chem. Int. Ed., 54, 8760-8763 (2015).

[18] Chiral Bronsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi-​Sakurai Allylation Reactions, Sai, M. Yamamloto, H., J. Am. Chem. Soc., 137,7091-7094 (2015).

[17] Nickel-​Catalyzed Regio- and Enantioselective Aminolysis of 3,​4-​Epoxy Alcohols, Wang, C.; Yamamoto, H.,  J. Am. Chem. Soc., 137, 4308-4311 (2015).

[16] Tungsten catalyzed oxidation and ring opening to generate >99.9%ee product, J. Am. Chem. Soc., 136, 1222-1225 (2014).

[15] Ten Years Research in Chicago, Tetrahedron, 69, 4503-4515 (2013).

[14] Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades. Angew. Chem124, 1978–1982 (2012).

[13] Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction of Tropones. J. Am. Chem. Soc., 131, 16628-16629 (2009).

[12] Dual-Activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed by a Tethered Bis(8-quinolinolato) Aluminum Complex. J. Am. Chem. Soc., 131, 15118-15119 (2009).

[11] Cationic-Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reaction of ,β-Unsaturated Acetylenic Ketones. Angew. Chem. Int. Ed., 48, 8060-8062 (2009).

[10] Catalytic Enantioselective Pudovik Reaction of Aldehydes and Aldimines with Tethers Bis(8-quinolinato) (TBOx) Aluminum Complex. J. Am. Chem. Soc., 130, 10521-10523 (2008).

[9] Regioselective and Asymetric Diels-Alder Reaction of 1- and 2-Substituted Cyclopentadienes Catalyzed by a Brønsted Acid Activated Chiral Oxazaborolidine, J. Am. Chem. Soc., 129, 9536-9537 (2007).

[8] Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-Quinolinolato) Aluminum Complexes, J. Am. Chem. Soc129, 742-743, (2007).

[7] Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and its application to Asymmetric Diels-Alder Reaction, J. Am. Chem. Soc128, 9626 (2006).

[6] Brønsted Acid Catalysis of Achiral Enamine for Regio- and Enantioselective Nitroso Aldol Synthesis. J. Am. Chem. Soc., 127, 1080 (2005).

[5] Oxazaborolidine-Derived Lewis Acid Assisted Lewis Acid as a Moisture-Tolerant Catalyst for Enantioselective Diels–Alder Reactions. Angew. Chem. Int. Ed. Enl., 44, 1484-1487 (2005).

[4] Designer Catalysis: Combined Acid Catalysis for Asymmetric Synthesis. Angew. Chem. Int. Ed44, 1924-1942 (2005).

[3] Acyloxyborane: An activating device for carboxylic acids. J. Am. Chem. Soc., 110, 6254 (1988).

[2] Asymmetric hetero-Diels-Alder reaction catalyzed by chiral organoaluminum reagent. J. Am. Chem. Soc., 110, 310 (1988).

[1] Asymmetric cyclization of unsaturated aldehydes catalyzed by a chiral Lewis acid. Tetrahedron Lett26, 5535, (1985).

    ^
Awards  

The Roger Adams Award, 2017

Fujiwara Prize, 2012

Noyori Prize, 2011

Member of American Academy of Arts and Sciences, 2011

Grand Prize of Synthetic Organic Chemistry of Japan, 2009

ACS Award for Creative Work in Synthetic Organic Chemistry, 2009

Honorary Member of the Chemical Society of Japan, 2008

The Japan Academy Award, 2007, Humboldt Research Award, 2007

The Karl-Ziegler Professorship, 2006

Tetrahedron Prize, 2006

Yamada Prize, 2004

Molecular Chirality Award, 2003, Fellow of American Association for the Advancement of Science, 2003

Tetrahedron Chair, 2002. Medal of Honor with Purple Ribbon (Japan), 2002

Max-Tishler Prize, 1998, Le Grand Prix de la Fondation Maison de la Chimie, 2002

The Chemical Society of Japan Award, 1995. Toray Science and Technology Award, 1997

Prelog Medal, 1993, Merck-Schuchardt Lectureship, 1994

IBM Science Award, 1988, Houkou Award, 1991, Chunichi Award, 1992

The Chemical Society of Japan Award for Young Chemist, 1977

    ^

Barluenga

  www.accio3.com