Expeditious synthesis of TADDOL-derived phosphoramidite and phosphonite ligands

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1232-1237

  Mewald, Marius ^a   Weickgenannt, Andreas ^a   Fröhlich, Roland ^a   Oestreich, Martin ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2,2,6,6 TETRAMETHYLPIPERIDIN 1 YL) 9,9 DIMETHYL 2,2,6,6 TETRAKIS(3,5 DIMETHYLPHENYL) 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0]DECANE; 4 (2,2,6,6 TETRAMETHYLPIPERIDIN 1 YL) 9,9 DIMETHYL 2,2,6,6 TETRAPHENYL 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0] DECANE; 4 (DIISOPROPYLAMINO) 9,9 DIMETHYL 2,2,6,6 TETRAPHENYL 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0]DECANE; 4 TERT BUTYL 2,2,6,6,9,9 HEXAPHENYL 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0]DECANE; 4 TERT BUTYL 9,9 DIMETHYL 2,2,6,6 TETRA (2 TOLYL) 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0]DECANE; 4 TERT BUTYL 9,9 DIMETHYL 2,2,6,6 TETRA(NAPHTHALEN 2 YL) 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO [5.3.0]DECANE; 4 TERT BUTYL 9,9 DIMETHYL 2,2,6,6 TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL] 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO [5.3.0]DECANE; 9,9 DIMETHYL 2,2,4,6,6 PENTA(NAPHTHALEN 2 YL) 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0]DECANE; 9,9 DIMETHYL 2,2,6,6 TETRAPHENYL 4 (7 PICOLYL) 3,5,8,10 TETRAOXA 4 PHOSPHABICYCLO[5.3.0]DECANE; CARBON; NITROGEN; NUCLEOPHILE; ORGANOPHOSPHORUS COMPOUND; PHOSPHONITE; PHOSPHORAMIDOUS ACID; PHOSPHORUS DERIVATIVE; PHOSPHORUS TRICHLORIDE; TADDOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS;

EID: 77956660169     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.010     Document Type: Article

References (32)

1. B.D. Chapsal, and I. Ojima New Methodologies and Techniques for a Sustainable Organic Chemistry NATO Science Series Vol. 246 2008 Springer Heidelberg 29 54
2. C. Claver, E. Fernandez, A. Gillon, K. Heslop, D.J. Hyett, A. Martorell, A.G. Orpen, and P.G. Pringle Chem. Commun. 2000 961 962
3. M.T. Reetz, and G. Mehler Angew. Chem., Int. Ed. 39 2000 3889 3890
4. M. van den Berg, A.J. Minnaard, E.P. Schudde, J. van Esch, A.H.M. de Vries, J.G. de Vries, and B.L. Feringa J. Am. Chem. Soc. 122 2000 11539 11540
5. For seminal contributions, see: J.-i. Sakaki, W.B. Schweizer, and D. Seebach Helv. Chim. Acta 76 1993 2654 2665
6. A. Alexakis, J. Frutos, and P. Mangeney Tetrahedron: Asymmetry 4 1993 2427 2430
7. A.H.M. de Vries, A. Meetsma, and B.L. Feringa Angew. Chem., Int. Ed. 35 1996 2374 2376
8. For authoritative reviews on asymmetric catalysis (allylic substitution, conjugate addition and hydrogenation) using BINOL-or TADDOL-derived monodentate phosphoramidites and phosphonites, see: A. Alexakis, J.E. Bäckvall, N. Krause, O. Pmies, and M. Diéguez Chem. Rev. 108 2008 2796 2823
9. B.L. Feringa Acc. Chem. Res. 33 2000 346 353
10. A.J. Minnaard, B.L. Feringa, L. Lefort, and J.G. de Vries Acc. Chem. Res. 40 2007 1267 1277
11. J.F. Teichert, and B.L. Feringa Angew. Chem., Int. Ed. 49 2010 2486 2528
12. For recent original publications, see: Hydrogenation: D. Peña, A.J. Minnaard, J.G. de Vries, and B.L. Feringa J. Am. Chem. Soc. 124 2002 14552 14553
13. Allene diboration: H.E. Burks, S. Liu, and J.P. Morken J. Am. Chem. Soc. 129 2007 8766 8773
14. C-H bond activation/arylation: M.R. Albicker, and N. Cramer Angew. Chem., Int. Ed. 48 2009 9139 9142
15. A. Weickgenannt, M. Mewald, T.W.T. Muesmann, and M. Oestreich Angew. Chem., Int. Ed. 49 2010 2223 2226
16. D. Seebach, M. Hayakawa, J.-i. Sakaki, and W.B. Schweizer Tetrahedron 49 1993 1711 1724
17. E. Keller, J. Maurer, R. Naasz, T. Schader, A. Meetsma, and B.L. Feringa Tetrahedron: Asymmetry 9 1998 2409 2413
18. A. Alexakis, J. Burton, J. Vastra, C. Benhaim, X. Fournioux, A. van den Heuvel, J.-M. Levêque, F. Mazé, and S. Rosset Eur. J. Org. Chem. 2000 4011 4027
19. D. Seebach, A.K. Beck, and A. Heckel Angew. Chem., Int. Ed. 40 2001 92 138
20. For the related BINOL-based, TMP-containing phosphoramidite, see: H. Du, W. Yuan, B. Zhao, and Y. Shi J. Am. Chem. Soc. 129 2007 11688 11689
21. D. Seebach, A.K. Beck, R. Imwinkelried, S. Roggo, and A. Wonnacott Helv. Chim. Acta 70 1987 954 974
22. C. Haase, C.R. Sarko, and M. DiMare J. Org. Chem. 60 1995 1777 1787
23. D. Seebach, R. Dahinden, R.E. Marti, A.K. Beck, D.A. Plattner, and F.N.M. Kuehnle J. Org. Chem. 60 1995 1788 1799
24. A.K. Beck, P. Gysi, L. La Vecchia, and D. Seebach Org. Synth. 76 1999 12 22
25. F. Toda, K. Tanaka, C.W. Leung, A. Meetsma, and B.L. Feringa J. Chem. Soc., Chem. Commun. 1994 2371 2372
26. A similar observation was made with a related phosphite: X. Linghu, J.R. Potnick, and J.S. Johnson J. Am. Chem. Soc. 126 2004 3070 3071
27. D. Seebach, A.K. Beck, R. Dahinden, M. Hoffmann, and F.N.M. Kühnle Croat. Chem. Acta 69 1996 459 484
28. J. Irurre, C. Alonso-Alija, J.F. Piniella, and A. Alvarez-Larena Tetrahedron: Asymmetry 3 1992 1591 1596
29. Z. Otwinowski, and W. Minor Methods Enzymol. 276 1997 307 326
30. Z. Otwinowski, D. Borek, W. Majewski, and W. Minor Acta Crystallogr., Sect. A 59 2003 228 234
31. G.M. Sheldrick Acta Crystallogr., Sect. A 46 1990 467 473
32. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112 122