Alkylation by asymmetric phase transfer catalysis
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Keiji Maruoka was born in 1953 in Mie, Japan. He graduated from Kyoto University (1976) and received his Ph.D. (1980) from University of Hawaii(Thesis Director: Prof. H. Yamamoto). He became an assistant professor of Nagoya University (1980) and was promoted to a lecturer (1985) and an associate professor (1990) there. He moved to Hokkaido University as a full professor (1995-2001), and he currently is a professor of chemistry in Kyoto University since 2000. (2007/2008). He is a board member of Chem. Commun. and is a member of the international advisory editorial board of Org. Biomol. Chem. And Chem. Asian J.

His current research interests include bidentate Lewis

acids in organic synthesis and practical asymmetric synthesis with chiral C2-symmetric phase-transfer catalysts and chiral bifunctional organocatalysts..

Keiji Maruoka,

Professor



Alkylation Amino Acid Synthesis


Pioneering work Amino Acid Synthesis

O’Donnell J. Am. Chem. Soc. 1989, 111, 2353.


Corey, E. J Amino Acid SynthesisJ. Am. Chem. Soc. 1997, 119, 12414.

Lygo, B. Tetrahedron Lett. 1997, 38, 8595.


almost all of the elaborated chiral phase-transfer catalysts reported so far have been restricted to cinchona alkaloid derivatives, which unfortunately constitutes a major difficulty in rationally designing and fine-tuning catalysts to attain sufficient reactivity and selectivity for various chemical transformations

under phase-transfer catalyzed conditions

Design new PTC catalyst which contain C2-Symmetry

J. Am. Chem. Soc. 1999, 121, 6519.


SYNLETT reported so far have been restricted to 2003, 12, 1931

Angew. Chem. Int. Ed. 2002, 41, 1551

T. A. 2003, 14, 1599


O.L. reported so far have been restricted to 2004, 6, 1429

Tetrahedron: Asymmetry 2004, 15, 1243

T.L. 2005, 46, 8555


classical reaction reported so far have been restricted to :

T. A. 2006,17, 603


Adv. Synth. Catal. reported so far have been restricted to 2002, No. 3+4, 344,


J. Am. Chem. Soc. reported so far have been restricted to 2000, 122, 5228.

Anaerobic Conditions is needed

Synlett 2001, 7, 1185


Facile synthesis of L-Dopa reported so far have been restricted to tert-butyl ester

Tetrahedron Lett. 2000, 41, 8339.


For two chiral binaphthyl catalysts are difficult for their fruitful modifications

They design more flexible one.

Angew. Chem. Int. Ed. 2002, 41, 1551


O.L. fruitful modifications2004, 6, 1429


Angew. Chem. Int. Ed. fruitful modifications2005, 44, 625


Angew. Chem. Int. Ed. fruitful modifications2005, 44, 1549

T.L. 2005, 46, 8555


Chem. Asian J. fruitful modifications2008, 3, 1702


Other Alkylation fruitful modifications

Angew. Chem. Int. Ed. 2003, 42, 3796


Angew. Chem. Int. Ed. fruitful modifications2003, 5,42


J. AM. CHEM. SOC. fruitful modifications 2005, 127, 5073


O.L. fruitful modifications2004, 7, 191


Adv. Synth. Catal. fruitful modifications2006, 348, 1539


Angew. Chem. Int. Ed. fruitful modifications2006, 45, 3839


O.L. fruitful modifications2007, 9,3945


T.L. fruitful modifications2008, 49, 5461

For pioneering work :Jew, S.-s. Org. Lett. 2005, 7, 1557.

Angew. Chem., Int. Ed. 2004, 43, 2383


Angew. Chem. Int. Ed. fruitful modifications2009, 48, 5014


Conclusion
conclusion fruitful modifications

  • design new powerful PTC catalyst which contain C2-Symmetry which is different from the cinchona skeleton

  • expand the application of the PTC in varieties of chemcal reaction


Thank you for your attention! fruitful modifications


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