Enantioselective desymmetrization of phospholene meso-epoxide by nucleophilic opening of the epoxide

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 41-45

  Pakulski, Zbigniew ^a   Pietrusiewicz, K Michał ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 4 AZIDO OXIDE; 3 HYDROXY 4 CYANOPHOSPHOLANE OXIDE; 3,4 EPOXY 1 PHENYLPHOSPHOLANE 1 OXIDE; ALKENE DERIVATIVE; ALUMINUM DERIVATIVE; AZIDE; CYANIDE; EPOXIDE; OXIDE; TRIMETHYLSILYL AZIDE; TRIMETHYLSILYL CYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; COMPLEX FORMATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RING OPENING;

EID: 0348048815     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.015     Document Type: Article

References (30)

1. (a) Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 2000;Springer, Berlin,
2. (b) Hodgson D.M., Gibbs A.R., Lee G.P. Tetrahedron. 52:1996;14361-14384.
3. Pietrusiewicz K.M., Zablocka M. Chem. Rev. 94:1994;1375-1411.
4. Pietrusiewicz K.M., Koprowski M., Pakulski Z. Tetrahedron: Asymmetry. 13:2002;1017-1019.
5. Pakulski Z., Kwiatosz R., Pietrusiewicz K.M. Tetrahedron Lett. 44:2003;5469-5472.
6. Bodalski R., Janecki T., Galdecki Z., Glówka M. Phosphorus Sulfur. 14:1982;15-21.
7. Quin L.D. The Heterocyclic Chemistry of Phosphorus. 1981;John Wiley, New York, Quin L.D. A Guide to Organophosphorus Chemistry. 2000;John Wiley, New York.
8. Quin L.D. The Heterocyclic Chemistry of Phosphorus. 1981;John Wiley, New York, Quin L.D. A Guide to Organophosphorus Chemistry. 2000;John Wiley, New York.
9. Arbuzov B.A., Anasteseva A.P., Vereschchagin A.N., Vizel A.O., Rakov A.P. Izv. Akad. Nauk SSSR, Ser. Khim. 1968;1729.
10. Symmes C., Quin L.D. Tetrahedron Lett. 1976;1853-1856.
11. (a) Yamamoto H., Inokawa S. Adv. Carbohydr. Chem. Biochem. 42:1984;135-191
12. (b) Yamamoto H., Hanaya T. Atta-ur-Rahman Studies in Natural Products Chemistry. Vol. 6:2000;351-384 Elsevier, Amsterdam
13. (c) Yamashita M., Yabui A., Suzuki K., Kato Y., Uchimura M., Iida A., Mizuno H., Ikai K., Oshikawa T. J. Carbohydr. Chem. 16:1997;499-519.
14. For the synthesis of phosphasugar N-isonucleoside derivatives from phospholane azides see: Yamashita M., Mallikarjuna Reddy P., Kato Y., Krishna Reddy V., Suzuki K., Oshikawa T. Carbohydr. Res. 336:2001;257-270.
15. Banaszek A., Pakulski Z., Zamojski A. Carbohydr. Chem. 279:1995;173-182.
16. Sabitha G., Babu R.S., Rajkumar M., Yadav J.S. Org. Lett. 4:2002;343-345.
17. Martínez L.E., Leighton J.L., Carsten D.H., Jacobsen E.N. J. Am. Chem. Soc. 117:1995;5897-5898.
18. Emziane M., Sutowardoyo K.I., Sinou D. J. Organomet. Chem. 346:1988;C7.
19. Sigman M.S., Jacobsen E.N. J. Am. Chem. Soc. 120:1998;5315-5316.
20. Song C.E., Oh C.R., Roh E.J., Choo D.J. Chem. Commun. 2000;1743-1744.
21. Demchuk, O. M.; Frelek, J.; Stankevič, M.; Świerczyń ska, W.; Pietrusiewicz, K. M, in press.
22. Sutowardoyo K.I., Sinou D. Tetrahedron: Asymmetry. 2:1991;437-444.
23. Schaus S.E., Jacobsen E.N. Org. Lett. 2:2000;1001-1004.
24. Nagata W., Yoshioka M., Okamura T. J. Chem. Soc. C. 1970;2365-2377.
25. In all cases studied no competing isocyanide formation was observed.
26. Δδ (Hz) is the separation of the signals of the two enantiomers.
27. Huddleston J.D., Willauer H.D., Swatloski R.P., Visser A.E., Rogers R.D. Chem. Commun. 1998;1765-1766.
28. Suarez P.A.Z., Dullius J.E.L., Einloft S., De Souza R.F., Dupont J. Polyhedron. 15:1996;1217-1219.
29. Bonhôte P., Dias A.P., Papageorgiou N., Kalyanasundaram K., Grätzel M. Inorg. Chem. 35:1996;1168-1178.
30. 3).