Direct Conversion of sec-Phosphine Oxides into Phosphinous Acid-Boranes

Synlett

Volumn , Issue 2, 2004, Pages 311-315

  Stankevič, Marek ^a   Andrijewski, Grzegorz ^b   Pietrusiewicz, K Michał ^a,c  

^a POLISH ACADEMY OF SCIENCES   (Poland)

^b UNIVERSITY OF LODZ   (Poland)

^c MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

Acidity; P stereogenic; Phosphinous acid boranes; sec phosphine oxides; Stereoselectivity

Indexed keywords

BORANE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHORUS ACID DERIVATIVE; REAGENT;

ARTICLE; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 1342323636     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815411     Document Type: Article

References (29)

1. (a) Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665.
2. (b) Ohff, H.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
3. (c) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197.
4. Corrbridge, D. E. C. In Phosphorus, an Outline of Its Chemistry, Biochemistry and Uses; Elsevier: Amsterdam, 1991.
5. Uziel, J.; Stephan, M.; Kaloun, E. B.; Genêt, J. P.; Jugé, S. Bull. Soc. Chim. Fr. 1997, 134, 379.
6. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417.(d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
7. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417. (d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
8. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417. (d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
9. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417. (d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
10. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417. (d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
11. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417. (d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
12. - see: (a) Jeno, T.; Ramsay-Shaw, B.; Porter, K.; Spielvogel, B. F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373. (b) He, K.; Hasan, A.; Krzyzanowska, B.; Ramsay-Shaw, B. J. Org. Chem. 1998, 63, 5769. (c) Sergueev, D. S.; Ramsay-Shaw, B. J. Am. Chem. Soc. 1998, 120, 9417. (d) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (e) Sergueeva, Z. A.; Sergueev, D. S.; Ramsay-Shaw, B. Tetrahedron Lett. 1999, 40, 2041. (f) Li, P.; Ramsay-Shaw, B. Chem. Commun. 2002, 2890. (g) Li, P.; Ramsay-Shaw, B. Org. Lett. 2002, 4, 2009.
13. Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185.
14. Köster, R.; Tsay, Y.-H.; Synoradzki, L. Chem. Ber. 1987, 120, 1117.
15. Stankevič, M.; Pietrusiewicz, K. M. Synlett 2003, 1012.
16. abstract
17. Reetz, T. J. Am. Chem. Soc. 1960, 82, 5039.
18. abstract
19. (a) Drabowicz, J.; Łyżwa, P.; Omelańczuk, J.; Pietrusiewicz, K. M.; Mikołajczyk, M. Tetrahedron: Asymmetry 1999, 10, 2757.
20. (b) Haynes, R. K.; Au-Yeung, T.-L.; Chan, W.-K.; Lam, W.-L.; Li, Z.-Y.; Yeung, L.-L.; Chan, A. S. C.; Li, P.; Koen, M.; Mitchell, C. R.; Vonwilier, S. C. Eur. J. Org. Chem. 2000, 3205.
21. (a) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
22. (b) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116.
23. Oshiki, T.; Hikosaka, T.; Imamoto, T. Tetrahedron Lett. 1991, 32, 3371.
24. (a) Motekajtis, R. J.; Martell, A. E. Can. J. Chem. 1982, 60, 168.
25. (b) Izquiedro, A.; Beltram, J. L. Anal. Chim. Acta 1986, 181, 87.
26. (c) Radomski, R.; Radomska, R.; Dankowski, M.; Szajowska, K.; Wisialski, Z. Comput. Chem. 1995, 19, 303.
27. Stankevič, M.; Pietrusiewicz, K. M. to be published.
28. (a) Kabachnik, M. I. Z. Chem. 1961, 1, 289.
29. (b) Kozachenko, A. G.; Uryupin, A. B.; Spivak, L. L.; Grigor'eva, A. A.; Matrosov, E. I.; Kabachnik, M. I.; Mastryukova, T. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 25, 1646.