Synthesis and application of new chiral ligands for the asymmetric borane reduction of prochiral ketones

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1373-1384

  Hulst, Ron ^a   Heres, Hero ^a   Peper, Nathalie C M W ^a   Kellogg, Richard M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

EID: 0029896043     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00154-1     Document Type: Article

References (41)

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12. For a review see: -Wallbaum, S., Martens, J., Tetrahedron: Asymmetry 1992, 12, 1475. -Deloux, L., Srebnik, M., Chem. Rev. 1993, 93, 763.
13. For a review see: -Wallbaum, S., Martens, J., Tetrahedron: Asymmetry 1992, 12, 1475. -Deloux, L., Srebnik, M., Chem. Rev. 1993, 93, 763.
14. Burns, B., Studley, J.R., Wills, M., Tetrahedron Lett. 1993, 34, 7105.
15. In contrast to trivalent phosphorus containing materials few pentavalent phosphoramides and phosphinamides have been used as chiral catalysts for enantioselective synthesis. For some good examples see: -Hanessian, S., Delorme, D., Beaudoin, S., LeBlanc, Y., J. Am. Chem. Soc. 1984, 106, 5754. -Soai, K., Hirose, Y., Ohno, Y., Tetrahedron: Asymmetry 1993, 4, 1473. -Soai, K., Ohno, Y., Inoue, Y., Tsuruoka, T., Hirose, T., Recl. Trv. Chim. Pays Bas 1995, 114, 145.
16. In contrast to trivalent phosphorus containing materials few pentavalent phosphoramides and phosphinamides have been used as chiral catalysts for enantioselective synthesis. For some good examples see: -Hanessian, S., Delorme, D., Beaudoin, S., LeBlanc, Y., J. Am. Chem. Soc. 1984, 106, 5754. -Soai, K., Hirose, Y., Ohno, Y., Tetrahedron: Asymmetry 1993, 4, 1473. -Soai, K., Ohno, Y., Inoue, Y., Tsuruoka, T., Hirose, T., Recl. Trv. Chim. Pays Bas 1995, 114, 145.
17. In contrast to trivalent phosphorus containing materials few pentavalent phosphoramides and phosphinamides have been used as chiral catalysts for enantioselective synthesis. For some good examples see: -Hanessian, S., Delorme, D., Beaudoin, S., LeBlanc, Y., J. Am. Chem. Soc. 1984, 106, 5754. -Soai, K., Hirose, Y., Ohno, Y., Tetrahedron: Asymmetry 1993, 4, 1473. -Soai, K., Ohno, Y., Inoue, Y., Tsuruoka, T., Hirose, T., Recl. Trv. Chim. Pays Bas 1995, 114, 145.
18. ten Hoeve, W., Wijnberg, H., Synthetic Commun. 1994, 6, 899.
19. ten Hoeve, W., Wynberg, H., J. Org. Chem. 1985, 50, 4508.
20. Poelert, M.A., Hof, R.P., Peper, N.C.M.W., Kellogg, R.M., Heterocycles 1994, 37, 461.
21. There are several examples of the use of amino thiols in asymmetric synthesis: -Hof, R.P., Poelert, M.A., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Kang, J., Lee, J.W., Kim, J.O., J. Chem. Soc., Chem. Commun. 1994, 2009. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
22. There are several examples of the use of amino thiols in asymmetric synthesis: -Hof, R.P., Poelert, M.A., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Kang, J., Lee, J.W., Kim, J.O., J. Chem. Soc., Chem. Commun. 1994, 2009. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
23. There are several examples of the use of amino thiols in asymmetric synthesis: -Hof, R.P., Poelert, M.A., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Kang, J., Lee, J.W., Kim, J.O., J. Chem. Soc., Chem. Commun. 1994, 2009. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
24. It should be noted that using the same methodology α-amino-γ-alcohols are also available: -Hulst, R., PhD Thesis, University of Groningen, 1994. -Hulst, R., Kellogg, R.M., Feringa, B.L., Recl. Trav. Chim. Pays Bas 1995, 114, 115.
25. It should be noted that using the same methodology α-amino-γ-alcohols are also available: -Hulst, R., PhD Thesis, University of Groningen, 1994. -Hulst, R., Kellogg, R.M., Feringa, B.L., Recl. Trav. Chim. Pays Bas 1995, 114, 115.
26. The shown configurations of 11 and 12 are chosen arbitrairely; the absolute configurations are not known.
27. Attempts to methylate 12 resulted in removal of the chlorine substituent.
28. Koning, B., Hulst, R., Kellogg, R.M., Recl. Trav. Chim. Pays Bas, 1996, 115, 49.
29. Atherton, F.R., Openshaw, H.T., Todd, A.R., J. Chem. Soc. 1945, 660.
30. -Hulst, R., de Vries, N.K., Feringa, B.L., Angew. Chem., Int. Ed. Engl. 1992, 31, 1092. -Hulst, R., Zijlstra, R.W.J., de Vries, N.K., Feringa, B.L., Tetrahedron: Asymmetry 1994, 5, 1701. -Hulst, R., de Vries, N.K., Feringa, B.L., Tetrahedron 1994, 50, 11721.
31. -Hulst, R., de Vries, N.K., Feringa, B.L., Angew. Chem., Int. Ed. Engl. 1992, 31, 1092. -Hulst, R., Zijlstra, R.W.J., de Vries, N.K., Feringa, B.L., Tetrahedron: Asymmetry 1994, 5, 1701. -Hulst, R., de Vries, N.K., Feringa, B.L., Tetrahedron 1994, 50, 11721.
32. -Hulst, R., de Vries, N.K., Feringa, B.L., Angew. Chem., Int. Ed. Engl. 1992, 31, 1092. -Hulst, R., Zijlstra, R.W.J., de Vries, N.K., Feringa, B.L., Tetrahedron: Asymmetry 1994, 5, 1701. -Hulst, R., de Vries, N.K., Feringa, B.L., Tetrahedron 1994, 50, 11721.
33. We could not separate the products by means of column chromatography, since cyclization takes place readily under these conditions.
34. Only one diastereomer was found, indicating that the cyclization occurs with high stereocontrol.
35. -Gorenstein, D.G., in Phosphorus-31 NMR Principles and Applications, Academic Press, New York, 1984. -Verkade, J.G., Quin, L.D., in Phosphorus-31 spectrocopy in Stereochemical Analysis, VCH Publishers, Deerfield Beach, 1987.
36. -Gorenstein, D.G., in Phosphorus-31 NMR Principles and Applications, Academic Press, New York, 1984. -Verkade, J.G., Quin, L.D., in Phosphorus-31 spectrocopy in Stereochemical Analysis, VCH Publishers, Deerfield Beach, 1987.
37. Although also other ketones can be reduced stereoselectively, propiophenone was used as the test ketone to obtain information about the reactivity and selectivity of several borane hydride complexes.
38. Hulst, R., de Vries, N.K., Feringa, B.L., Tetrahedron: Asymmetry 5, 699, 1994.
39. Hulst, R., Heres, H., Kellogg, R.M., manuscript in preparation.
40. The ligands can also be used for the addition of diethylzinc to aldehydes; -Hulst, R., Heres, H., Fitzpatrick, K., Peper, N.C.M.W., Kellogg, R.M., manuscript in preparation.
41. 3): 68.09 ppm.