New indenyl phosphinooxazoline complexes of iron and their catalytic activity in the Mukaiyama aldol reaction

Tetrahedron Letters

Volumn 51, Issue 21, 2010, Pages 2855-2858

  Lenze, Matthew ^a   Sedinkin, Sergey L ^a   Rath, Nigam P ^a   Bauer, Eike B ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

Catalysis; Indenyl ligand; Iron complexes; Mukaiyama aldol reaction; Phosphinooxazolines

Indexed keywords

1 (TERT BUTYLDIMETHYLSILYLOXY) 1 METHOXYETHENE; ALDEHYDE; ETHYLENE DERIVATIVE; IRON; OXAZOLE DERIVATIVE; PHOSPHINOOXAZOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; MUKAIYAMA REACTION; SYNTHESIS;

EID: 77950934502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.090     Document Type: Article

References (45)

1. Czaplik W.M., Mayer M., Cvengroš J., and Jacobi von Wangelin A. ChemSusChem 2 (2009) 396
2. Fürstner A. Angew. Chem., Int. Ed. 48 (2009) 1364
3. Bauer E.B. Curr. Org. Chem. 12 (2008) 1341
4. Enthaler S., Junge K., and Beller M. Angew. Chem., Int. Ed. 47 (2008) 3317
5. Correra A., Garcia Mancheño O., and Bolm C. Chem. Soc. Rev. 37 (2008) 1108
6. Sherry B.D., and Fürstner A. Acc. Chem. Res. 41 (2008) 1500
7. Gaillard S., and Renaud J.-L. ChemSusChem 1 (2008) 505
8. Díaz Díaz D., Miranda P.O., Padròn J.I., and Martín V.S. Curr. Org. Chem. 10 (2006) 457
9. Bolm C., Legros J., Le Paih J., and Zani L. Chem. Rev. 104 (2004) 6217
10. Costas M., Mehn M.P., Jensen M.P., and Que Jr. L. Chem. Rev. 104 (2004) 939
11. Garrett C.E., and Prasad K. Adv. Synth. Catal. 346 (2004) 889
12. Gelalcha F.G., Anilkumar G., Tse M.K., Brückner A., and Beller M. Chem. Eur. J. 14 (2008) 7687
13. Nakanishia M., and Bolm C. Adv. Synth. Catal. 349 (2007) 861
14. Casey C.P., and Guan H. J. Am. Chem. Soc. 131 (2009) 2499
15. Czaplik W.M., Mayer M., and Jacobi von Wangelin A. Angew. Chem., Int. Ed. 48 (2009) 607
16. Cahiez G., Foulgoc L., and Moyeux A. Angew. Chem., Int. Ed. 48 (2009) 2969-2972
17. Loska R., Rao Volla C.M., and Vogel P. Adv. Synth. Catal. 350 (2008) 2859
18. Correa A., Carril M., and Bolm C. Angew. Chem., Int. Ed. 47 (2008) 2880
19. Wu J.-R., Lin C.-H., and Lee C.-F. Chem. Commun. (2009) 4450
20. Tomov A.K., Gibson V.C., Britovsek G.J.P., Long R.L., van Meurs M., Jones D.J., Tellmann K.P., and Chirinos J.J. Organometallics 28 (2009) 7033
21. Han W., and Ofial A.R. Chem. Commun. (2009) 6023
22. García Mancheño O., Dallimore J., Plant A., and Bolm C. Adv. Synth. Catal. 352 (2010) 309
23. von Matt P., and Pfaltz A. Angew Chem., Int. Ed. Engl. 32 (1993) 566
24. Sprinz J., and Helmchen G. Tetrahedron Lett. 34 (1993) 1769
25. Dawson G.J., Frost C.G., Williams J.M., and Coote S.J. Tetrahedron Lett. 34 (1993) 3149
26. Recent examples:. Bélanger E., Pouliot M.-F., and Paquin J.-F. Org. Lett. 11 (2009) 2201
27. Popa D., Marcos R., Sayalero S., Vidal-Ferran A., and Pericás M.A. Adv. Synth. Catal. 351 (2009) 1539
28. Sedinkin S.L., Rath N.P., and Bauer E.B. J. Organomet. Chem. 693 (2008) 3081
29. Lenze M., and Bauer E.B. J. Mol. Catal. A: Chem. 309 (2009) 117
30. O'Connor J.M., and Casey C.P. Chem. Rev. 87 (1987) 307
31. Rerek M.E., Ji L.-N., and Basolo F.J. Chem. Soc., Chem. Commun. (1983) 1208
32. Calhorda M.J., Romão C.C., and Veiros L.F. Chem. Eur. J. 8 (2002) 868
33. Xu X., Chen Y., Feng J., Zou G., and Sun J. Organometallics 29 (2010) 549
34. Garrett C.E., and Fu G.C. J. Org. Chem. 63 (1998) 1370
35. Mukaiyama T., Narasaka K., and Banno K. Chem. Lett. (1973) 1011
36. Mukaiyama T., Banno K., and Narasaka K. J. Am. Chem. Soc. 96 (1974) 7504
37. Jones D.J., and Mawby R.J. Inorg. Chim. Acta 6 (1972) 157
38. Belmont J.A., and Wrighton M.S. Organometallics 5 (1986) 1421 and literature cited therein
39. 6 Ligand 1c was synthesized following an identical protocol, and experimental details are given in Supplementary data.
40. Derrah E.J., Marlinga J.C., Mitra D., Friesen D.M., Hall S.A., McDonald R., and Rosenberg L. Organometallics 24 (2005) 5817
41. Garcia M.H., Robalo M.P., Teixeira A.P.S., Piedade M.F.M., and Duarte M.T. J. Organomet. Chem. 632 (2001) 145
42. -3. Experimental details and crystallographic data for the X-ray determination can be found in Supplementary data.
43. Nishiyama Y., Kaiba K., and Umeda R. Tetrahedron Lett. 51 (2010) 793
44. Han J.S., Kim S.B., and Mukaiyama T. Bull. Korean Chem. Soc. 15 (1994) 529
45. Bach T., Fox D.N.A., and Reetz M.T. J. Chem. Soc., Chem. Commun. (1992) 1634