Alkylation by Asymmetric Phase-Transfer Catalysis

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Alkylation by Asymmetric Phase-TransferCatalysis

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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
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• Design of Chiral Phase Transfer Catalysts for
  Practical Amino Acid Synthesis
• Design of Chiral Organocatalysts for Practical
  Asymmetric Synthesis Bronsted Acid Catalysts
• Development of Bidentate Lewis Acid Chemistry and
  Application to Selective Organic Synthesis

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Alkylation
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Pioneering work
ODonnell J. Am. Chem. Soc. 1989, 111, 2353.
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Corey, E. J J. Am. Chem. Soc. 1997, 119, 12414.
Lygo, B. Tetrahedron Lett. 1997, 38, 8595.
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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.
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SYNLETT 2003, 12, 1931
Angew. Chem. Int. Ed. 2002, 41, 1551
T. A. 2003, 14, 1599
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O.L. 2004, 6, 1429
Tetrahedron Asymmetry 2004, 15, 1243
T.L. 2005, 46, 8555
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classical reaction
T. A. 2006, 17, 603
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Adv. Synth. Catal. 2002, No. 34, 344,
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J. Am. Chem. Soc. 2000, 122, 5228.
Anaerobic Conditions is needed
Synlett 2001, 7, 1185
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Facile synthesis of L-Dopa tert-butyl ester
Tetrahedron Lett. 2000, 41, 8339.
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For two chiral binaphthyl catalysts are difficult
for their fruitful modifications They design more
flexible one.
Angew. Chem. Int. Ed. 2002, 41, 1551
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O.L. 2004, 6, 1429
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Angew. Chem. Int. Ed. 2005, 44, 625
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Angew. Chem. Int. Ed. 2005, 44, 1549
T.L. 2005, 46, 8555
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Chem. Asian J. 2008, 3, 1702
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Other Alkylation
Angew. Chem. Int. Ed. 2003, 42, 3796
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Angew. Chem. Int. Ed. 2003, 5, 42
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J. AM. CHEM. SOC. 2005, 127, 5073
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O.L. 2004, 7, 191
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Adv. Synth. Catal. 2006, 348, 1539
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Angew. Chem. Int. Ed. 2006, 45, 3839
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O.L. 2007, 9, 3945
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T.L. 2008, 49, 5461
For pioneering work Jew, S.-s. Org. Lett. 2005,
7, 1557. Angew.
Chem., Int. Ed. 2004, 43, 2383
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Angew. Chem. Int. Ed. 2009, 48, 5014
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conclusion

• 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

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Thank you for your attention!