Diastereoselective addition of organolithiums to 1,3-oxazolidines complexed with aluminum tris(2,6-diphenylphenoxide) (ATPH)

Tetrahedron

Volumn 61, Issue 7, 2005, Pages 1731-1736

  Yamauchi, Takayasu ^a   Sazanami, Hiroyuki ^a   Sasaki, Yuuichi ^a   Higashiyama, Kimio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

Allylic strain; Iminium aluminum complex; Lewis acid; NOE experiment; Phenylglycinol

Indexed keywords

ALUMINUM DERIVATIVE; ALUMINUM TRIS(2,6 DIPHENYLPHENOXIDE); LEWIS ACID; ORGANOLITHIUM COMPOUND; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; GRIGNARD REACTION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 12944308800     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.12.036     Document Type: Article

References (29)

1. For reviews on organometallic additions to imine and their derivatives, see: (a) D. Enders, and U. Reinhold Tetrahedron: Asymmetry 8 1997 1895 1946
2. R. Bloch Chem. Rev. 98 1998 1407 1438
3. G. Alvaro, and D. Savoia Synlett 2002 651 673
4. G. Martelli, and D. Savoia Curr. Org. Chem. 7 2003 1049 1070
5. H. Takahashi, B.C. Hsieh, and K. Higashiyama Chem. Pharm. Bull. 38 1990 2429 2434
6. K. Higashiyama, H. Inoue, T. Yamauchi, and H. Takahashi J. Chem. Soc., Perkin Trans. 1 1995 111 115
7. T. Yamauchi, H. Takahashi, and K. Higashiyama Chem. Pharm. Bull. 46 1998 384 389
8. T. Yamauchi, H. Takahashi, and K. Higashiyama Heterocycles 48 1998 1813 1823
9. A. Ishii, F. Miyamoto, K. Higashiyama, and K. Mikami Tetrahedron Lett. 39 1998 1199 1202
10. H. Poerwono, K. Higashiyama, and H. Takahashi J. Org. Chem. 63 1998 2711 2714
11. K. Maruoka, H. Imoto, S. Saito, and H. Yamamoto J. Am. Chem. Soc. 116 1994 4131 4132
12. K. Maruoka, M. Ito, and H. Yamamoto J. Am. Chem. Soc. 117 1995 9091 9092
13. T. Ooi, T. Miura, Y. Kondo, and K. Maruoka Tetrahedron Lett. 38 1997 3947 3950
14. T. Ooi, Y. Kondo, K. Kon-I, and K. Maruoka Chem. Lett. 1998 403 404
15. S. Saito, T. Sone, K. Shimada, and H. Yamamoto Synlett 1999 81 83
16. A. Marx, and H. Yamamoto Synlett 1999 584 586
17. S. Saito, M. Shiozawa, and H. Yamamoto Angew. Chem., Int. Ed. 38 1999 1769 1771
18. S. Saito, S. Yamazaki, and H. Yamamoto Angew. Chem., Int. Ed. 40 2001 3613 3617
19. S. Saito, M. Nagahara, M. Shiozawa, H. Nakadai, and H. Yamamoto J. Am. Chem. Soc. 125 2003 6200 6210
20. H. Ito, T. Nagahara, K. Ishihara, S. Saito, and H. Yamamoto Angew. Chem., Int. Ed. 43 2004 994 997
21. S. Denmark, and M. Seierstad J. Org. Chem. 64 1999 1610 1619
22. S. Kanemasa, N. Ueno, and M. Shirahase Tetrahedron Lett. 43 2002 657 660
23. H. Takahashi, Y. Suzuki, and T. Kametani Heterocycles 20 1983 607 610
24. H. Takahashi, H. Niwa, and K. Higashiyama Heterocycles 27 1988 2099 2102
25. L.N. Pridgen J. Org. Chem. 56 1991 1340 1344
26. K. Higashiyama, H. Inoue, and H. Takahashi Tetrahedron 50 1994 1083 1092
27. H. Poerwono, K. Higashiyama, T. Yamauchi, and H. Takahashi Heterocycles 46 1997 385 400
28. H. Poerwono, K. Higashiyama, T. Yamauchi, H. Kubo, S. Ohmiya, and H. Takahashi Tetrahedron 54 1998 13955 13970
29. 1H NMR spectrum on 1′ and 2′ position of 4h was determined.