Synthesis of oxazolidinones initiated by regio- and diastereo-controlled crotylation of α-dicarbonyl compounds

Organic and Biomolecular Chemistry

Volumn 8, Issue 9, 2010, Pages 2009-2011

  Shibata, Ikuya ^a   Kojima, Ryota ^a   Tsunoi, Shinji ^a   Nozaki, Takashi ^b   Watanabe, Tomonari ^b   Ninomiya, Atsushi ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

^b ASAHI KASEI CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATIONS; CARBON-CARBON BOND FORMATION; DICARBONYL COMPOUNDS; ONE-POT SYNTHESIS; OXAZOLIDINONES; SIDE CHAINS;

COMPLEXATION;

KETONE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

KETONES; MOLECULAR STRUCTURE; OXAZOLIDINONES; STEREOISOMERISM;

EID: 77951123849     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c000197j     Document Type: Article

References (35)

1. M. E. Dyen D. Swern Chem. Rev. 1967 67 197 246
2. S. Ozaki Chem. Rev. 1972 72 457 456
3. M. Raimond C. Bertolotti E. Orlandini C. Oro G. Sartori M. Selva Tetrahedron Lett. 2007 48 2131 2134
4. G. Cardillo M. Orena S. Sandri C. Tomashini Tetrahedron 1987 43 2505 2512
5. A. V. Rama Rao T. G. Murali Dhar T. K. Chakraborty M. K. Gurjar Tetrahedron Lett. 1988 29 2069 2072
6. M. R. Barbachn D. K. Hutchinson S. J. Brickner G. E. Zurenko J. Med. Chem. 1996 39 680 685
7. R. T. Lewis A. M. Macleod K. J. Merchant F. Kelleher I. Sanderson R. H. Herbert M. A. Cascieri S. Sadowski R. G. Ball K. Hoogsteen J. Med. Chem. 1995 38 923 933
8. B. M. Kim J. P. Guare C. M. Hanifin D. J. Arford-Bickerstaff J. P. Vacca R. G. Ball Tetrahedron Lett. 1994 35 5153 5156
9. Y. Yamamoto N. Asao Chem. Rev. 1993 93 2207 2293
10. W. R. Roush, in Comprehensive Organic Synthesis, Vol. 2, ed.:, B. M. Trost, and, I. Fleming, Pergamon Press, Oxford, 1991, Chapter 1.1, pp 1
11. Y. Nishigaichi A. Takuwa Tetrahedron 1993 49 7395 7426
12. J. A. Marshall Chem. Rev. 1996 96 31 48
13. E. J. Thomas, in Stereoselective Synthesis, Vol. 3, ed.:, G. Helmchen, R. W. Hoffmann, J. Mulzer, and, E. Schaumann, Georg Thieme, Stuttgart, 1996, Chapter 1.3.3.3.6, pp 1508-1540
14. Y. Yamamoto Acc. Chem. Res. 1987 20 243 249
15. E. W. Abel D. A. Armitage D. B. Brady Trans. Faraday Soc. 1966 62 3459 3462
16. A. Baba, I. Shibata and M. Yasuda, in Comprehensive Organometallic Chemistry III, Vol. 9, Chapter 8, ed., R. H. Crabtree, D. Michael, and, P. Mingos, Elsevier, Oxford, 2006, pp. 341-380
17. M. Pereyre, P. J. Quintard and A. Rahm, in Tin in Organic Synthesis, Butterworth, London, 1987
18. A. G. Davies, in Organotin Chemistry, VCH, Weinhelm, 1997
19. I. Shibata H. Kato N. Kanazawa M. Yasuda A. Baba J. Am. Chem. Soc. 2004 126 466 467
20. B. M. Santoyo C. González-Romero O. Merino R. Martínez- Palou A. Fuentes-Benites H. A. Jiménez-Vázquez F. Delgado J. Tamariz Eur. J. Org. Chem. 2009 2505 2518
21. C. Gonzalez-Romero P. Bernal F. Jimenez M. Carmen Cruz A. Fuentes-Benites A. Benavides R. Bautista J. Tamariz Pure Appl. Chem. 2007 79 181 191
22. K. Yano A. Baba H. Matsuda Bull. Chem. Soc. Jpn. 1992 65 66 70
23. A. J. Bloodworth A. G. Davies S. C. Vasishtha J. Chem. Soc. C 1967 1309 1313
24. P. G. Harrison J. J. Zuckerman Inorg. Chem. 1970 9 175 181
25. D. P. Agur G. Srivastaka R. C. Mehrostra Ind. J. Chem. 1974 12 1193
26. S. Sakai M. Miura N. Wada T. Fujinami Bull. Chem. Soc. Jpn. 1983 56 1873 1874
27. H. Yasuda J.-C. Choi S.-C. Lee T. Sakakura J. Organomet. Chem. 2002 659 133 141
28. A. Baba H. Kishiki I. Shibata H. Matsuda Organometallics 1985 4 1329 1333
29. I. Shibata K. Nakamura A. Baba Matsuda Bull. Chem. Soc. Jpn. 1989 62 853 859
30. A. Gambaro D. Marton G. Tagliavini J. Organomet. Chem. 1981 210 57 61
31. A. Boaretto D. Marton G. Tagliavini J. Organomet. Chem. 1987 321 199 207
32. H. Miyake K. Yamamura Chem. Lett. 1992 1369 1372
33. V. J. Jephcote E. J. Thomas Tetrahedron Lett. 1985 26 5327 5330
34. A. Gambaro P. Gains D. Marton V. Peruzzo G. Tagliavini J. Organomet. Chem. 1982 231 307 314
35. D. Hoppe, in Stereoselective Synthesis, Vol. 3, Chapter 1.3.3, ed.:, G. Helmchen, R. W. Hoffmann, J. Mulzer, and, E. Schaumann, Georg Thieme, Stuttgart, 1996, pp 1357-1368