Catalytic enantioselective alkylation of benzaldehyde with diethylzinc using chiral nonracemic (thio)-phosphoramidates

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2755-2760

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

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZALDEHYDE; PHOSPHORAMIDIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030250102     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00355-2     Document Type: Article

References (29)

1. 1. -Noyori, R., Kitamura, M., Angew. Chem., Int. Ed. Engl. 1991, 30, 49. -Soai, K., Niwa, S., Chem. Rev. 1992, 92, 833.
2. 1. -Noyori, R., Kitamura, M., Angew. Chem., Int. Ed. Engl. 1991, 30, 49. -Soai, K., Niwa, S., Chem. Rev. 1992, 92, 833.
3. 2. -Chaloner, P.A., Renuka Perera, S.A., Tetrahedron Lett. 1987, 28, 3013. -Kitamura, M., Suga, S., Kawai, K., Noyori, R., J. Am. Chem. Soc. 1986, 108, 6071. -Smaardijk, A.A., Wynberg, H., J. Org. Chem. 1987, 52, 135. -Soai, K., Yokoyama, S., Hayasaka, T., J. Org. Chem. 1991, 56, 4264.
4. 2. -Chaloner, P.A., Renuka Perera, S.A., Tetrahedron Lett. 1987, 28, 3013. -Kitamura, M., Suga, S., Kawai, K., Noyori, R., J. Am. Chem. Soc. 1986, 108, 6071. -Smaardijk, A.A., Wynberg, H., J. Org. Chem. 1987, 52, 135. -Soai, K., Yokoyama, S., Hayasaka, T., J. Org. Chem. 1991, 56, 4264.
5. 2. -Chaloner, P.A., Renuka Perera, S.A., Tetrahedron Lett. 1987, 28, 3013. -Kitamura, M., Suga, S., Kawai, K., Noyori, R., J. Am. Chem. Soc. 1986, 108, 6071. -Smaardijk, A.A., Wynberg, H., J. Org. Chem. 1987, 52, 135. -Soai, K., Yokoyama, S., Hayasaka, T., J. Org. Chem. 1991, 56, 4264.
6. 2. -Chaloner, P.A., Renuka Perera, S.A., Tetrahedron Lett. 1987, 28, 3013. -Kitamura, M., Suga, S., Kawai, K., Noyori, R., J. Am. Chem. Soc. 1986, 108, 6071. -Smaardijk, A.A., Wynberg, H., J. Org. Chem. 1987, 52, 135. -Soai, K., Yokoyama, S., Hayasaka, T., J. Org. Chem. 1991, 56, 4264.
7. 3. -Hof, R.P., Poelert, M.P., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Rijnberg, E., Jastrzebski, J.T.B.H., Janssen, M.D., Boersma, J., van Koten, G., Tetrahedron Lett. 1994, 35, 6521. -Kang, J., Lee, J.W., Kim, J.I., J. Chem. Soc., Chem. Commun. 1994, 2009. -Kang, J., Kim, D.S., Kim, J.I., Synlett 1994, 842. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
8. 3. -Hof, R.P., Poelert, M.P., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Rijnberg, E., Jastrzebski, J.T.B.H., Janssen, M.D., Boersma, J., van Koten, G., Tetrahedron Lett. 1994, 35, 6521. -Kang, J., Lee, J.W., Kim, J.I., J. Chem. Soc., Chem. Commun. 1994, 2009. -Kang, J., Kim, D.S., Kim, J.I., Synlett 1994, 842. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
9. 3. -Hof, R.P., Poelert, M.P., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Rijnberg, E., Jastrzebski, J.T.B.H., Janssen, M.D., Boersma, J., van Koten, G., Tetrahedron Lett. 1994, 35, 6521. -Kang, J., Lee, J.W., Kim, J.I., J. Chem. Soc., Chem. Commun. 1994, 2009. -Kang, J., Kim, D.S., Kim, J.I., Synlett 1994, 842. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
10. 3. -Hof, R.P., Poelert, M.P., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Rijnberg, E., Jastrzebski, J.T.B.H., Janssen, M.D., Boersma, J., van Koten, G., Tetrahedron Lett. 1994, 35, 6521. -Kang, J., Lee, J.W., Kim, J.I., J. Chem. Soc., Chem. Commun. 1994, 2009. -Kang, J., Kim, D.S., Kim, J.I., Synlett 1994, 842. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
11. 3. -Hof, R.P., Poelert, M.P., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1994, 5, 31. -Rijnberg, E., Jastrzebski, J.T.B.H., Janssen, M.D., Boersma, J., van Koten, G., Tetrahedron Lett. 1994, 35, 6521. -Kang, J., Lee, J.W., Kim, J.I., J. Chem. Soc., Chem. Commun. 1994, 2009. -Kang, J., Kim, D.S., Kim, J.I., Synlett 1994, 842. -Fitzpatrick, K., Hulst, R., Kellogg, R.M., Tetrahedron: Asymmetry 1995, 6, 1861.
12. 4. Recently, also autocatalytic enantioselective alkylation was reported: -Soai, K., Shibata, T., Morioka, H., Choji, K., Nature 1995, 378, 767. -Shibata, T., Morioka, H., Hayase, T., Choji, K., Soai, K., J. Am. Chem. Soc. 1996, 110, 471.
13. 4. Recently, also autocatalytic enantioselective alkylation was reported: -Soai, K., Shibata, T., Morioka, H., Choji, K., Nature 1995, 378, 767. -Shibata, T., Morioka, H., Hayase, T., Choji, K., Soai, K., J. Am. Chem. Soc. 1996, 110, 471.
14. 5. -Ito, K., Kimura, H., Okamura, H., Katsuki, T., Synlett. 1992, 573. -Rozema, M.J., AchyuthaRao, S., Knochel, P., J. Org. Chem. 1992, 57, 1956. -Eisenberg, C., Knochel, P., J. Org. Chem. 1994, 59, 3760.
15. 5. -Ito, K., Kimura, H., Okamura, H., Katsuki, T., Synlett. 1992, 573. -Rozema, M.J., AchyuthaRao, S., Knochel, P., J. Org. Chem. 1992, 57, 1956. -Eisenberg, C., Knochel, P., J. Org. Chem. 1994, 59, 3760.
16. 5. -Ito, K., Kimura, H., Okamura, H., Katsuki, T., Synlett. 1992, 573. -Rozema, M.J., AchyuthaRao, S., Knochel, P., J. Org. Chem. 1992, 57, 1956. -Eisenberg, C., Knochel, P., J. Org. Chem. 1994, 59, 3760.
17. 6. -Schmidt, B., Seebach, D., Angew. Chem., Int. Ed. Engl. 1991, 30, 99. -Schmidt, B., Seebach, D., Angew. Chem., Int. Ed. Engl. 1991, 30, 1321. -Seebach, D., Beck, A.K., Schmidt, B., Wang, Y.M., Tetrahedron 1994, 50, 4363.
18. 6. -Schmidt, B., Seebach, D., Angew. Chem., Int. Ed. Engl. 1991, 30, 99. -Schmidt, B., Seebach, D., Angew. Chem., Int. Ed. Engl. 1991, 30, 1321. -Seebach, D., Beck, A.K., Schmidt, B., Wang, Y.M., Tetrahedron 1994, 50, 4363.
19. 6. -Schmidt, B., Seebach, D., Angew. Chem., Int. Ed. Engl. 1991, 30, 99. -Schmidt, B., Seebach, D., Angew. Chem., Int. Ed. Engl. 1991, 30, 1321. -Seebach, D., Beck, A.K., Schmidt, B., Wang, Y.M., Tetrahedron 1994, 50, 4363.
20. 7. -Soai, K., Hirose, Y., Ohno, Y., Tetrahedron: Asymmetry 1993, 4, 1473. -Soai, K., Ohno, Y., Inoue, Y., Tsuruoka, T., Hirose, T., Recl. Trav. Chim. Pays Bas 1995, 114, 145.
21. 7. -Soai, K., Hirose, Y., Ohno, Y., Tetrahedron: Asymmetry 1993, 4, 1473. -Soai, K., Ohno, Y., Inoue, Y., Tsuruoka, T., Hirose, T., Recl. Trav. Chim. Pays Bas 1995, 114, 145.
22. 8. -ten Hoeve, W., Wynberg, H., J. Org. Chem. 1985, 50, 4508. -ten Hoeve, W., Wynberg, H., Synthetic Commun. 1994, 6, 899.
23. 8. -ten Hoeve, W., Wynberg, H., J. Org. Chem. 1985, 50, 4508. -ten Hoeve, W., Wynberg, H., Synthetic Commun. 1994, 6, 899.
24. 9. Hulst, R., Heres, H., Peper, N.C.M.W., Kellogg, R.M., Tetrahedron: Asymmetry 1996, 5, 1373.
25. 10. Koning, B., Hulst, R., Kellogg, R.M., Recl. Trav. Chim. Pays Bas 1996, 115, 49.
26. 11. Poelert, M.A., Hof, R.P., Peper, N.C.M.W., Kellogg, R.M., Heterocycles 1994, 37, 461.
27. 12. Hulst, R., de Vries, N.K., Feringa, B.L., Tetrahedron: Asymmetry 1994, 5, 699.
28. 13. The configurations shown for 8 and 9 are arbitrary; the absolute configurations are not known.
29. 14. Hulst, R., Kellogg, R.M., Feringa, B.L., Recl. Trav. Chim. Pays Bas 1995, 114, 115.