Generation and amplification of optical activity of axially chiral N-(1-naphthyl)-2(1H)-pyrimidinethione by crystallization

Organic and Biomolecular Chemistry

Volumn 8, Issue 23, 2010, Pages 5418-5422

  Sakamoto, Masami ^a   Yagishita, Fumitoshi ^a   Ando, Masaru ^a   Sasahara, Yuich ^a   Kamataki, Norifumi ^a   Ohta, Mai ^a   Mino, Takashi ^a   Kasashima, Yoshio ^a   Fujita, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOND ROTATIONS; HIGH TEMPERATURE; NON-POLAR SOLVENTS; OPTICAL ACTIVITY; PROTIC SOLVENTS; SOLVENT PROPERTIES; SPACE GROUPS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

CRYSTALLIZATION; SINGLE CRYSTALS;

SOLVENTS;

EID: 78149429448     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00262c     Document Type: Article

References (33)

1. E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 1142
2. G. Bringmann A. J. P. Mortimer P. A. Keller M. J. Gresser J. Garner M. Breuning Angew. Chem., Int. Ed. 2005 44 5384 5427
3. Asymmetric Synthesis (ed.:, R. A. Aitkin,,, S. N. KilLnyi,), Blackie, Glasgow, 1992
4. Asymmetric Synthesis, Vols. 1-5 (Ed.:, J. D. Morrison,), Academic Press, Orlando, 1983-1985
5. Methods of Organic Chemistry (Houben-Weyl), Vol. 21a-f (ed.:, G. Helmchen,,, R. W. Hoffmann,,, J. Mulzer,,, E. Schaumann,), Thieme, New York, 1995
6. Comprehensive Asymmetric Catalysis I-III (ed.:, E. N. Jacobsen,)
7. R. Noyori, Asymmeric Catalysis in Organic Synthesis, Wiley, New York, 1994
8. J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995
9. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Comprehensive Asymmetric Synthesis I-III, Springer, Berlin, 2000
10. R. E. Pincock R. R. Perkins A. S. Ma K. R. Wilson Science 1971 174 1018 1020
11. M. Sakamoto N. Utsumi M. Ando M. Saeki T. Mino T. Fujita A. Katoh T. Nishio C. Kashima Angew. Chem., Int. Ed. 2003 42 4360 4363
12. C. Viedma Phys. Rev. Lett. 2005 94 065504
13. W. L. Noorduin T. Izumi A. Millemaggi M. Leeman H. Meekes W. J. P. van Enckevort R. M. Kellogg B. Kaptein E. Vlieg D. G. Blackmond J. Am. Chem. Soc. 2008 130 1158
14. W. L. Noorduin H. Meekes W. J. P. van Enckevort A. Millemaggi M. Leeman B. Kaptein R. M. Kellogg E. Vlieg Angew. Chem., Int. Ed. 2008 47 6445
15. B. Kaptein W. L. Noorduin H. Meekes W. J. P. van Enckevort R. M. Kellogg E. Vlieg Angew. Chem., Int. Ed. 2008 47 7226
16. C. Viedma J. E. Ortiz T. de Torres T. Izumi D. G. Blackmond J. Am. Chem. Soc. 2008 130 15274
17. S. B. Tsogoeva S. Wei M. Freund M. Mauksch Angew. Chem., Int. Ed. 2009 48 590
18. C. Viedma Astrobiology 2007 7 312
19. J. H. E. Cartwright O. Piro I. Tuval Phys. Rev. Lett. 2007 98 165501
20. W. L. Noorduin H. Meekes A. A. C. Bode W. J. P. van Enckevort B. Kaptein R. M. Kellogg E. Vlieg Cryst. Growth Des. 2008 8 1675
21. W. L. Noorduin P. Van DerAsdonk H. Meekes W. J. P. van Enckevort B. Kaptein M. Leeman R. M. Kellogg E. Vlieg Angew. Chem., Int. Ed. 2009 48 3278
22. B. Norden Nature 1977 266 567
23. L. Addadi and M. Lahav, Origin of Optical Activity in Nature, Ed.:, D. C. Walker
24. S. F. Mason Nature 1997 389 804
25. S. F. Mason Nature 1984 311 19 23
26. J. Bailey, A. Chrysostomou, J. H. Hough, T. M. Gledhill, A. McCall, S. Clark, F. Menard and M. Tamura, Science, 1998, 281, 672. Elsevier, New York, 1979, chap. 14
27. Crystallization induced diastereomer transformation (CIDT) of axially chirality was also performed. M. Sakamoto A. Unosawa S. Kobaru Y. Hasegawa T. Mino Y. Kasashima T. Fujita Chem. Commun. 2007 1632 1634
28. M. Sakamoto N. Sato T. Mino Y. Kasashima T. Fujita Org. Biomol. Chem. 2008 6 848 850
29. A. S. Cooke M. M. Harris J. Chem. Soc. 1963 2365 2373
30. C. Kashima A. Katoh J. Chem. Soc., Perkin Trans. 1 1980 1599 1602
31. C. Roussel M. Adjimi A. Chemlal A. Djafri J. Org. Chem. 1988 53 5076 5080
32. H. Schirok C. Alonso-Alija J. Benet-Buchholz A. H. Göller R. Grosser M. Michels H. Paulsen J. Org. Chem. 2005 70 9463 9469
33. D. K. Kondepudi J. Laudadio K. Asakura J. Am. Chem. Soc. 1999 121 1448 1451