An Approach to Asymmetric Synthesis of New Pyridine Aminophosphine Oxides. Preparation of the Diastereomerically Pure 1-(Pyridine-3-yl)-1-[N-(alfa- methyl benzyl amino)]-methyl-diphenylphosphine Oxides and 1-(Pyridine-3-yl)-1-[N-(alfa-methylbenzylamino)]

• Autorzy: Guzik M. , Olszewski T. K. , Boduszek B.
• Języki publikacji: PL

Abstrakty

EN

A series of diastereomerically pure aminophosphine oxides derived from pyridine- 3-carboxaldehyde and chiral amine was synthesized. The aminophosphine oxides were obtained by an addition reaction of the diphenylphosphine oxide or racemic t-butylphenylphosphine oxide to the optically active, corresponding chiral aldimines, which were obtained from pyridine-3-carboxaldehyde and enantiomers of alfa-methyl benzyl - amine. The formed diastereomers were easy separated by crystallization from acetone.

Słowa kluczowe

EN

pyridine-3-carboxaldehyde; alfa-methylbenzylamine; diphenylphosphine oxide; t-butyl-phenylphosphine oxide; aldimines; addition reaction; diastereomers

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 11
• Strony: 1879--1885
• Opis fizyczny: Bibliogr. 6 poz., rys.

Twórcy

autor

Guzik M.

autor

Olszewski T. K.

autor

Boduszek B.

• Department of Organic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland

Bibliografia

• l. Goldeman W., Olszewski T.K., Boduszek B. and Sawka-Dobrowolska W., Tetrahedron, 62, 4506 (2006).
• 2. Boduszek B., Olszewski T., Goldeman W. and Konieczna M., Phosphorus, Sulfur and Silicon, 181, 787 (2006).
• 3. Boduszek B., Synth Commun., 33, 4087 (2003).
• 4. Szabo A., Jaszay Z.M., Hegedus L., Toke L. and Petnehazy L, Tetrahedron Lett., 44, 4603 (2003).
• 5. a) Hoffmann H. and Schellenbeck P, Chem. Ber., 99, 1134 (1966); b) Drabowicz J., Łyżwa P, Omelanczuk J., Pietrusiewicz K.M. and Mikołajczyk M., Tetrahedron Asym., 10, 2757 (1999).
• 6. Busacca C.A., Lorens J.C., Grinberg N., Haddad N., Hrapchak M., Latli B., Lee H., Sabina P, Saha A., Sarvestani M, Shen S., Varsolona R., Wei X. and Senanayake C., Organic Letters, 7(19), 4277 (2005).