Asymmetric Michael reaction: novel efficient access to chiral β-ketophosphonates

Tetrahedron Asymmetry

Volumn 18, Issue 5, 2007, Pages 685-691

  Delarue Cochin, Sandrine ^a,b   Pan, Jian Jung ^c   Dauteloup, Aurélie ^a,b   Hendra, Frédéric ^a,b   Angoh, Roger Gagali ^a,b   Joseph, Delphine ^a,b   Stephens, Philip J ^c   Cavé, Christian ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

^c UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALPHA METHYLBENZYLAMINE; BETA KETOPHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARBUZOV REACTION; ARTICLE; CHIRALITY; DENSITY FUNCTIONAL THEORY; DEPROTECTION REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MICHAEL ADDITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PINNER REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSESTERIFICATION; X RAY ANALYSIS;

EID: 33947721060     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.02.023     Document Type: Article

References (27)

1. Pinheiro S., Guingant A., Desmaële D., and d'Angelo J. Tetrahedron: Asymmetry 3 (1992) 1003
2. Gassama A., d'Angelo J., Cavé C., Mahuteau J., and Riche C. Eur. J. Org. Chem. (2000) 3165
3. Nour M., Tan K., Jankowski R., and Cavé C. Tetrahedron: Asymmetry 12 (2001) 765
4. Christoffers J., and Baro A. Angew. Chem., Int. Ed. 42 (2003) 1688
5. Arai S., Tokumaru K., and Aoyama T. Chem. Pharm. Bull. 52 (2004) 646
6. Hendra F., Nour M., Baglin I., Morgant G., and Cavé C. Tetrahedron: Asymmetry 15 (2004) 1027
7. Hendra, F. Ph.D. Dissertation, Université de Bourgogne, Dijon, France, 2005.
8. Varlet J.M., and Collignon N. Tetrahedron 37 (1981) 3713
9. Zymanczyk-Duda E., Lejczak B., and Kafarski P. Tetrahedron 43 (1995) 11809
10. Ordonez M., de la Cruz R., Fernandez-Zertuche M., and Munoz-Hernandez M.-A. Tetrahedron: Asymmetry 13 (2002) 559
11. Nesterov V.V., and Kolodiazhnyi O.I. Tetrahedron: Asymmetry 17 (2006) 1023
12. Ladame S., Bardet M., Périé J., and Wilson M. Bioorg. Med. Chem. 9 (2001) 773
13. Greco M.N., Hawkins M.J., Powell E.T., Almond Jr. H.R., Corcoran T.W., de Garavilla L., Kauffman J.A., Recacha R., Chattopadhyay D., Andrade-Gordon P., and Maryanoff B.E. J. Am. Chem. Soc. 124 (2002) 3810
14. Li X., Bhandari A., Holmes C.P., and Szardenings A.K. Bioorg. Med. Chem. Lett. 14 (2004) 4301
15. Bernier S., Akochy P.-M., Lapointe J., and Chênevert R. Bioorg. Med. Chem. 13 (2005) 69
16. Sevin A., Tortajada J., and Pfau M. J. Org. Chem. 51 (1986) 2671
17. Corbel B., Medinger L., Haelters J.-P., and Sturtz G. Synthesis (1985) 1048
18. Saadi M., Lebeau L., and Miokowski C. Helv. Chim. Acta 78 (1995) 670
19. Cohen R.J., Fox D.L., Eubank J.F., and Salvatore R.N. Tetrahedron Lett. 44 (2003) 8617
20. Yao Z.-J., Gao Y., and Burke Jr. T.R. Tetrahedron: Asymmetry 10 (1999) 3727
21. Schwartz A., and Madan P. J. Org. Chem. 51 (1986) 5463
22. Pizzonero M., Hendra F., Delarue-Cochin S., Tran Huu Dau M.-E., Dumas F., Cavé C., Nour M., and d'Angelo J. Tetrahedron: Asymmetry 16 (2005) 3853
23. Stephens P.J., and Devlin F.J. Chirality 12 (2000) 172
24. Stephens P.J. In: Bultinck P., de Winter H., Langenaecker W., and Tollenaere J. (Eds). Computational Medicinal Chemistry for Drug Discovery (2003), Dekker, New York 699-725 Chapter 26
25. Cere V., Peri F., Pollicino S., Ricci A., Devlin F.J., Stephens P.J., Gasparrini F., Rompietti R., and Villani C. J. Org. Chem. 70 (2005) 664
26. Carosati E., Cruciani G., Chiarini A., Budriesi R., Ioan P., Spisani R., Spinelli D., Cosimelli B., Fusi F., Frosini M., Matucci R., Gasparrini F., Ciogli A., Stephens P.J., and Devlin F.J. J. Med. Chem. 49 (2006) 5206
27. gaussian 03, Gaussian Inc. www.gaussian.com.