Addition of secondary phosphines to a vinyl ether of diacetone-d-glucose: A new approach to optically active phosphines and their derivatives

Tetrahedron Letters

Volumn 45, Issue 49, 2004, Pages 9143-9145

  Trofimov, Boris A ^a   Sukhov, Boris G ^a   Malysheva, Svetlana F ^a   Belogorlova, Natal'ya A ^a   Tantsirev, Anatolii P ^a   Parshina, Lidiya N ^a   Oparina, Ludmila A ^a   Tunik, Sergey P ^a   Gusarova, Nina K ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

Addition; Optically active tertiary phosphines; Phosphine oxides and sulfides; Radical initiation; Secondary phosphines; Vinyl ether of diacetone d glucose

Indexed keywords

DIACETONE DEXTRO GLUCOSE; ETHER DERIVATIVE; GLUCOSE DERIVATIVE; OXIDE; OXYGEN; PHOSPHINE DERIVATIVE; SULFUR; UNCLASSIFIED DRUG; VINYL ETHER;

ADDITION REACTION; ARTICLE; MOLECULAR INTERACTION; OPTICAL ROTATION; OXIDATION; QUANTITATIVE ANALYSIS; QUANTUM YIELD; RADICAL REACTION; REACTION ANALYSIS;

EID: 8644229188     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.172     Document Type: Article

References (23)

1. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 John Wiley & Sons New York
2. E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Berlin
3. I. Ojima Catalytic Asymmetric Synthesis 2nd ed. 2000 VCH Weinheim
4. W. Petltkowska, M. Gouygou, J.-C. Daran, G. Balavoine, and M. Mikolajczyk Tetrahedron Lett. 42 2001 12 17
5. H. Brunner Top. Stereochem. 18 1988 129 247
6. P. Braunstein, and F. Naud Angew. Chem., Int. Ed. 40 2001 680 699
7. I.V. Komorov, A. Spannenbeg, J. Hoz, and A. Burner Chem. Commun. 2003 2240 2241
8. C.P. Casey, E.L. Paulsen, E.W. Beuttenmueller, B.R. Proft, B.A. Matter, and D.R. Powell J. Am. Chem. Soc. 121 1999 63 70
9. D.J. Brauer, K.W. Kottsieper, T. Nickel, O. Stelzer, and W.S. Sheldrick Eur. J. Inorg. Chem. 2001 1251 1259
10. T. Bunlaksananusorn, and P. Knochel Tetrahedron Lett. 43 2002 5817 5819
11. B.D. Dombek J. Org. Chem. 43 1978 3408 3409
12. S.F. Malysheva, N.K. Gusarova, N.A. Belogorlova, M.V. Nikitin, D.V. Gendin, and B.A. Trofimov Zh. Obshch. Khim. 67 1997 63 66
13. B.A. Trofimov, N.K. Gusarova, S.F. Malysheva, N.I. Ivanova, B.G. Sukhov, N.A. Belogorlova, and V.A. Kuimov Synthesis 2002 2207 2210
14. B.A. Trofimov, S.F. Malysheva, B.G. Sukhov, N.A. Belogorlova, E.Yu. Schmidt, L.N. Sobenina, V.A. Kuimov, and N.K. Gusarova Tetrahedron Lett. 44 2003 2629 2632
15. N.K. Gusarova, S.F. Malysheva, N.A. Belogorlova, S.N. Arbuzova, D.V. Gendin, and B.A. Trofimov Zh. Org. Khim. 33 1997 1231 1234
16. B.I. Mikhant'ev, and V.L. Lapenko Zh. Obshch. Khim. 27 1957 2840 2841
17. 2), 105.02 (C-1), 108.98 and 111.76 (C-7,8), 149.94 (CHO)
18. W.A.P. Black, E.T. Dewar, and D. Rutherford J. Chem. Soc. 1963 4433 4439
19. S.N. Arbuzova, L. Brandsma, N.K. Gusarova, and B.A. Trofimov Recl. Trav. Chim. Pays-Bas 113 1994 575 576
20. B.A. Trofimov, L. Brandsma, S.N. Arbuzova, S.F. Malysheva, and N.K. Gusarova Tetrahedron Lett. 35 1994 7647 7650
21. 6P (528.62): C, 68.17; H, 7.82; P, 5.86%. Found: C, 68.39; H, 7.73; P, 5.65%
22. 7P (544.62): C, 66.16; H, 7.59; P, 5.69%. Found: C, 66.22; H, 7.32; P, 5.85%
23. 6PS (560.69): C, 64.27; H, 7.37; P, 5.52; S, 5.72%. Found: C, 64.45; H, 7.55; P, 5.35; S, 5.58%