Synthesis and application in asymmetric C-C bond formation of solution phase ligand libraries of monodentate phosphoramidites

Organic and Biomolecular Chemistry

Volumn 2, Issue 12, 2004, Pages 1682-1684

  Duursma, Ate ^a   Lefort, Laurent ^b   Boogers, Jeroen A F ^b   De Vries, André H M ^b   De Vries, Johannes G ^a,b   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CHEMICAL BONDS; ESTERS; ETHANOL; NUCLEAR MAGNETIC RESONANCE; POTASSIUM COMPOUNDS; RHODIUM; SCREENING; SOLUTIONS; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

BOND FORMATION; ENONES; LIGAND LIBRARIES; MONODENTATE PHOSPHORAMIDITES;

AROMATIC COMPOUNDS;

EID: 3042789542     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404996a     Document Type: Article

References (26)

1. (a) J. G. de Vries and A. H. M. de Vries, Eur. J. Org. Chem., 2003, 799;
2. (b) C. Gennari and U. Piarulli, Chem. Rev., 2003, 103, 3071.
3. D. L. Coffen and J. E. A. Luithle, in Handbook of Combinatorial Chemistry, eds. K. C. Nicolaou, R. Hanko and W. Hartwig, Wiley-VCH, Weinheim, 2002, vol. 1, p. 10.
4. (a) B. Jandeleit, D. Schaefer, T. S. Powers, H. W. Turner and W. H. Weinberg, Angew. Chem., Int. Ed., 1999, 38, 2494;
5. (b) M. T. Reetz, Angew. Chem., Int. Ed., 2001, 40, 284.
6. (a) M. T. Reetz, Angew. Chem., Int. Ed., 2002, 41, 1335;
7. (b) A. Duursma, A. J. Minnaard and B. L. Feringa, Tetrahedron, 2002, 58, 5773.
8. N. E. Leadbeater and M. Marco, Chem. Rev., 2002, 102, 3217.
9. (a) O. Huttenloch, E. Laxman and H. Waldmann, Chem. Commun., 2002, 673;
10. (b) S. Doherty, E. G. Robins, I. Pál, C. R. Newman, C. Hardacre, D. Rooney and D. A. Mooney, Tetrahedron: Asymmetry, 2003, 14, 1517;
11. (c) A. Mandoli, M. Calamante, B. L. Feringa and P. Salvadori, Tetrahedron: Asymmetry, 2003, 14, 3647.
12. J. G. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481.
13. L. Lefort, J. A. F. Boogers, A. H. M. de Vries and J. G. de Vries, Org. Lett., 2004, 6, 1733.
14. For the 1,4-addition of arylboronic acids using phosphoramidite based catalysts see: (a) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 681; (b) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 1385; (c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 3111; (d) J. G. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481; (e) Y. Iguchi, R. Itooka and N. Miyaura, Synlett, 2003, 7, 1040. Further details of the 1,4-addition of vinyltrifluoroborate will be published in due course.
15. For the 1,4-addition of arylboronic acids using phosphoramidite based catalysts see: (a) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 681; (b) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 1385; (c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 3111; (d) J. G. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481; (e) Y. Iguchi, R. Itooka and N. Miyaura, Synlett, 2003, 7, 1040. Further details of the 1,4-addition of vinyltrifluoroborate will be published in due course.
16. For the 1,4-addition of arylboronic acids using phosphoramidite based catalysts see: (a) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 681; (b) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 1385; (c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 3111; (d) J. G. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481; (e) Y. Iguchi, R. Itooka and N. Miyaura, Synlett, 2003, 7, 1040. Further details of the 1,4-addition of vinyltrifluoroborate will be published in due course.
17. For the 1,4-addition of arylboronic acids using phosphoramidite based catalysts see: (a) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 681; (b) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 1385; (c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 3111; (d) J. G. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481; (e) Y. Iguchi, R. Itooka and N. Miyaura, Synlett, 2003, 7, 1040. Further details of the 1,4-addition of vinyltrifluoroborate will be published in due course.
18. For the 1,4-addition of arylboronic acids using phosphoramidite based catalysts see: (a) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 681; (b) J. G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 1385; (c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 3111; (d) J. G. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481; (e) Y. Iguchi, R. Itooka and N. Miyaura, Synlett, 2003, 7, 1040. Further details of the 1,4-addition of vinyltrifluoroborate will be published in due course.
19. (a) M. Pucheault, S. Darses and J. P. Genet, Eur. J. Org. Chem., 2002, 3552;
20. (b) S. Oi, A. Taira, Y. Honma and Y. Inoue, Org. Lett., 2003, 5, 97.
21. This reactor was developed by Premex in cooperation with DSM, see: www.premex-reactorag.ch/e/specialloesungen/produkteneuheiten.
22. The poorer results with sterically hindered phosphorochloridite C are not the result of incomplete ligand formation as was evident from NMR analysis.
23. T. T.-L. Au-Yeung, S.-S. Chan and A. S. C. Chan, Adv. Synth. Catal., 2003, 345, 537.
24. (a) M. T. Reetz, T. Sell, A. Meiswinkel and G. Mehler, Angew. Chem., Int. Ed., 2003, 42, 790;
25. (b) D. Peña, A. J. Minnaard, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries and B. L. Feringa, Org. Biomol. Chem., 2003, 1, 1087;
26. (c) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 3111.