Highly enantioselective addition of diethylzinc to N-diphenylphosphinylimines using dendritic chiral ligands with hydrocarbon backbones

Tetrahedron Asymmetry

Volumn 11, Issue 11, 2000, Pages 2271-2275

  Sato, Itaru ^a   Kodaka, Ryo ^a   Shibata, Takanori ^a   Hirokawa, Yutaka ^a   Shirai, Nobuaki ^a   Ohtake, Koji ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINOALCOHOL; DENDRIMER; DIETHYLZINC; HYDROCARBON; IMINE; LIGAND; N DIPHENYLPHOSPHINYLAMINE; N DIPHENYLPHOSPHINYLIMINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034674726     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00194-4     Document Type: Article

References (45)

1. (a) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663;
2. (b) Hecht, S.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 4084-4085.
3. For reviews, see: (c) Tomalia, D. A.; Naylor, A. M.; Goddard III, W. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138-175;
4. (d) Newkome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichim. Acta 1992, 25, 31-38;
5. (e) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688;
6. (f) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 884-905.
7. (a) Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413;
8. (b) Leininger, S.; Stang, P. J.; Huang, S. Organometallics 1998, 17, 3981-3987.
9. Gossage, R. A.; Jastrzebski, J. T. B. H.; van Ameijde, J.; Mulders, S. J. E.; Brouwer, A. J.; Liskamp, R. M. J.; van Koten, G. Tetrahedron Lett. 1999, 40, 1413-1416;
10. (b) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529.
11. For example, see: (a) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Polym. Adv. Technol. 1999, 10, 30-38; (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304-310; (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918-1920; (d) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837-842.
12. For example, see: (a) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Polym. Adv. Technol. 1999, 10, 30-38; (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304-310; (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918-1920; (d) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837-842.
13. For example, see: (a) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Polym. Adv. Technol. 1999, 10, 30-38; (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304-310; (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918-1920; (d) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837-842.
14. For example, see: (a) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Polym. Adv. Technol. 1999, 10, 30-38; (b) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J. M. J. J. Org. Chem. 1990, 55, 304-310; (c) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1918-1920; (d) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837-842.
15. (a) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740;
16. (b) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563-1570;
17. (c) Köllner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275.
18. For the ligands with one chiral site possessing dendritic substituents, see: (a) Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387-388; (b) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032; (c) Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221-3236; (d) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536; (e) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285-2296.
19. For the ligands with one chiral site possessing dendritic substituents, see: (a) Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387-388; (b) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032; (c) Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221-3236; (d) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536; (e) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285-2296.
20. For the ligands with one chiral site possessing dendritic substituents, see: (a) Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387-388; (b) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032; (c) Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221-3236; (d) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536; (e) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285-2296.
21. For the ligands with one chiral site possessing dendritic substituents, see: (a) Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387-388; (b) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032; (c) Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221-3236; (d) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536; (e) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285-2296.
22. For the ligands with one chiral site possessing dendritic substituents, see: (a) Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387-388; (b) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032; (c) Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221-3236; (d) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536; (e) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285-2296.
23. Suzuki, T.; Hirokawa, Y.; Ohtake, K.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 4033-4040.
24. Sato, I.; Shibata, T.; Ohtake, K.; Kodaka, R.; Hirokawa, Y.; Shirai, N.; Soai, K. Tetrahedron Lett. 2000, 41, 3123-3126.
25. (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681-6684;
26. (b) Katritzky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437-442;
27. (c) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797-8798.
28. (d) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489-8490;
29. (e) Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, K.; Inomata, K. Chem. Lett. 1997, 59-60;
30. (f) Watanabe, K.; Kuroda, S.; Yokoi, A.; Ito, K.; Itsuno, S. J. Organomet. Chem. 1999, 581, 103-107;
31. (g) Chen, G.-M.; Ramachandran, V.; Brown, H. C. Angew. Chem., Int. Ed. 1999, 38, 825-826.
32. For reviews, see: (h) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946;
33. (i) Denmark, S. E.; Nicaise, O. J.-C.; Chem. Commun. 1996, 999-1004.
34. For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
35. For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
36. (a) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097-1098;
37. (b) Hayase, T.; Inoue, Y.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2509-2510.
38. For application by others, see: (c) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364-7375.
39. (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317-318;
40. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519-2522;
41. (c) Suzuki, T.; Shibata T.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1997, 2757-2760.
42. (a) Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357-1370;
43. (b) Protective Groups in Organic Synthesis, 3rd ed.; Green, T. W.; Wutz, P. G. M.; John Wiley & Sons: New York, 1999; p. 598.
44. 3OH).
45. The enantioselective addition of diethylzinc to imine 3a in the presence of 1.0 mol. equiv. of (1R,2S)-N-benzylephedrine for 24 h gave the corresponding (R)-amine 4a with 92% e.e. in the yield of 91%. It should be noted that, in the reaction using chiral ligand 2, a lesser amount of chiral ligand 2 (0.17 mol. equiv.) was utilized (Table 1, Entry 8).