Synthesis of chiral γ-amino-β-hydroxyphosphonate derivatives from unsaturated phosphonates

Synlett

Volumn , Issue 14, 2004, Pages 2505-2508

  Yamagishi, Takehiro ^a   Fujii, Keiichi ^a   Shibuya, Shiroshi ^a   Yokomatsu, Tsutomu ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Asymmetric synthesis; Dihydoxylations; Phosphorus; Regioselectivity; Sulfates

Indexed keywords

CARNITINE DERIVATIVE; GAMMA AMINO BETA HYDROXYPHOSPHONATE DERIVATIVE; OSMIUM; PHOSPHONIC ACID DERIVATIVE; SULFATE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; OPTICAL ROTATION; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; TECHNIQUE;

EID: 9644300939     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834792     Document Type: Article

References (27)

1. Golay, A.; Swislocki, A. L. M.; Chen, Y. D.; Reaven, G. M. Metabolism 1987, 36, 692.
2. McGarry, J. D.; Brown, N. F. Eur. J. Biochem. 1997, 244, 1.
3. For a review, see: Giannessi, F. Drugs Future 2003, 28, 371.
4. (a) Giannessi, F.; Chiodi, P.; Marzi, M.; Minetti, P.; Pessotto, P.; De Angelis, F.; Tassoni, E.; Conti, R.; Giorgi, F.; Mabilia, M.; Dell'Uomo, N.; Muck, S.; Tinti, M. O.; Carminati, P.; Arduini, A. J. Med. Chem. 2001, 44, 2383.
5. (b) Giannessi, F.; Pessotto, P.; Tassoni, E.; Chiodi, P.; Conti, R.; De Angelis, F.; Dell'Uomo, N.; Catini, R.; Deias, R.; Tinti, M. A.; Carminati, P.; Arduini, A. J. Med. Chem. 2003, 46, 303.
6. (a) Ordóñez, M.; González-Morales, A.; Ruiz, C.; De la Cruz-Cordero, R.; Fernández-Zertuche, M. Tetrahedron: Asymmetry 2003, 14, 1775.
7. (b) Mikolajczyk, M.; Luczak, J.; Kielbasinski, P. J. Org. Chem. 2002, 67, 7872.
8. (c) Wróblewski, A. E.; Halajewska-Wosik, A. Eur. J. Org. Chem. 2002, 2758.
9. (d) Tadeusiak, E.; Krawiecka, B.; Michalski, J. Tetrahedron Lett. 1999, 40, 1791.
10. (e) Ordóñez, M.; De la Cruz, R.; Fernández-Zertuche, M.; Muñoz-Hernández, M.-A. Tetrahedron: Asymmetry 2002, 13, 559.
11. (f) Thomas, A. A.; Sharpless, K. B. J. Org. Chem. 1999, 64, 8379.
12. For a review, see: Kolb, H. C.; van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
13. (a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365.
14. (b) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767.
15. Lonray and co-workers reported similar AD reactions independently. See: Lonray, B. B.; Maji, D. K.; Nandanan, E. Indian J. Chem., Sect. B 1995, 34, 1023.
16. Yokomatsu, T.; Yamagishi, T.; Sada, T.; Suemune, K.; Shibuya, S. Tetrahedron 1998, 54, 781.
17. 2O (0.8 mol%) was critical for AD reactions of β,γ-unsaturated phosphonates since the AD reaction of 2b in the absence of the osmium salt resulted in slow reaction rates (20 h at 25 °C) and slight decrease in enantioselectivity (54% yield, 30% ee).
18. +]: 399.1185. Found: 399.1185.
19. (a) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805.
20. (b) Corey, E. J.; Noe, M. C.; Guzman-Perez, A. J. Am. Chem. Soc. 1995, 117, 10817.
21. Kobayashi and co-workers observed that a related AD of α-olefins with dibenzyl phosphonate showed higher enantioselectivity than the corresponding diethyl phosphonate. See: Kobayashi, Y.; William, A. D.; Tokoro, Y. J. Org. Chem. 2001, 66, 7903.
22. +]: 351.1361. Found: 351.1352.
23. (a) Lohray, B. B. Synthesis 1992, 1035.
24. (b) Bittman, R.; Byun, H.-S.; He, L. Tetrahedron 2000, 56, 7051.
25. Gao, Y.; Sharpless, K. B. J. Org. Chem. 1988, 110, 7538.
26. +]: 464.2386. Found: 464.2382.
27. 3) of 13, a signal ascribed to the Me group at the γ-position was observed at δ = 1.18 ppm as a doublet (J = 7.1 Hz) but not as a singlet corresponding to regioisomeric β-amino-γ-ketophosphonate (Scheme 7). (Diagram presented)