1,2,3,4,5,6-Hexahydrophosphinine 1-oxides with an exocyclic P-function at position 3: Diastereoselective synthesis, stereostructure and conformation

Tetrahedron Letters

Volumn 46, Issue 10, 2005, Pages 1655-1658

  Keglevich, György ^a   Sipos, Melinda ^a   Körtvélyesi, Tamás ^b   Imre, Tímea ^c   Toke, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Conformation; Hydrogenation; Phosphorus heterocycles; Stereoselection

Indexed keywords

EXOCYCLIC DOUBLE BOND; OXIDE; PHOSPHINE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONFORMATION; CROSS COUPLING REACTION; DIASTEREOISOMER; HYDROGENATION; HYDROGENOLYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 13744260318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.073     Document Type: Article

References (16)

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3. Gy. Keglevich, M. Sipos, T. Imre, K. Ludányi, D. Szieberth, and L. Toke Tetrahedron Lett. 43 2002 8515 8518
4. Gy. Keglevich, M. Sipos, D. Szieberth, L. Nyulászi, T. Imre, K. Ludányi, and L. Toke Tetrahedron 60 2004 6619 6627
5. Gy. Keglevich, M. Sipos, D. Szieberth, Gy. Petocz, and L. Kollár J. Organomet. Chem. 689 2004 3158 3162
6. General procedure for the preparation of 3-substituted-5-methyl-1-phenyl or 1-alkoxy-1,2,3,4,5,6-hexahydrophosphinine 1-oxides (4a, 5a, b and 6a,b): A solution of 0.10 g of the 3-substituted-1,2,3,6-tetrahydrophosphinine 1-oxide (1a, 2a, b, 3a,b) in 30 ml of methanol was measured in an autoclave equipped with a magnetic stirrer and 0.10 g of 10% Pd/C was added. The hydrogenation was carried out at 45°C and at 3 bar for 14 h for 1a and at 25°C and 2.5 bar for 14 h for the other starting materials (2a, b and 3a, b). The resulting suspension was filtered and the solvent was evaporated. Purification of the crude product by column chromatography (silica gel, 3% methanol in chloroform) afforded the hexahydrophosphinine oxide in the cases of 4a, 5a and 6a as a single isomer, or in the cases of 5b and 6b, as a mixture of diastereomers
7. Gy. Keglevich, A. Kovács, K. Újszászy, A. Tungler, G. Tóth, and L. Toke Phosphorus Sulfur 70 1992 219 227
8. 2 requires 409.1486
9. 2 requires 317.1072
10. 2 requires 345.1384
11. 3)
12. 3)
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14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann Jr., J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98, Revision A.7 1998 Gaussian Pittsburgh PA
15. Ab initio calculations were performed at the HF/6-31G* level with full geometry optimisation. The force constants were found to be positive in the minima
16. Gy. Keglevich, A. Kovács, and L. Toke ACH-Models in Chem. 131 1994 513 520