Alkylation by Asymmetric Phase-Transfer Catalysis

1. Alkylation by Asymmetric Phase-TransferCatalysis 张文全

2. 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

3. 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

5. Alkylation

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

7. Corey, E. J J. Am. Chem. Soc. 1997, 119, 12414. Lygo, B. Tetrahedron Lett. 1997, 38, 8595.

8. 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.

9. SYNLETT2003, 12, 1931 Angew. Chem. Int. Ed. 2002, 41, 1551 T. A. 2003, 14, 1599

10. O.L. 2004, 6, 1429 Tetrahedron: Asymmetry 2004, 15, 1243 T.L. 2005, 46, 8555

11. classical reaction： T. A. 2006,17, 603

12. Adv. Synth. Catal. 2002, No. 3+4, 344,

13. J. Am. Chem. Soc. 2000, 122, 5228. Anaerobic Conditions is needed Synlett 2001, 7, 1185

14. Facile synthesis of L-Dopa tert-butyl ester Tetrahedron Lett. 2000, 41, 8339.

15. For two chiral binaphthyl catalysts are difficult for their fruitful modifications They design more flexible one. Angew. Chem. Int. Ed. 2002, 41, 1551

16. O.L. 2004, 6, 1429

17. Angew. Chem. Int. Ed. 2005, 44, 625

18. Angew. Chem. Int. Ed. 2005, 44, 1549 T.L. 2005, 46, 8555

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20. Other Alkylation Angew. Chem. Int. Ed. 2003, 42, 3796

21. Angew. Chem. Int. Ed. 2003, 5,42

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23. O.L. 2004, 7, 191

24. Adv. Synth. Catal. 2006, 348, 1539

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26. O.L. 2007, 9,3945

27. T.L. 2008, 49, 5461 For pioneering work :Jew, S.-s. Org. Lett. 2005, 7, 1557. Angew. Chem., Int. Ed. 2004, 43, 2383

28. Angew. Chem. Int. Ed. 2009, 48, 5014

29. 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

30. Thank you for your attention!