Lanthanoid triflate-promoted indium- or zinc-mediated allylation of aminoaldehyde in aqueous media: Stereoselective route to β-aminoalcohols

Main Group Metal Chemistry

Volumn 20, Issue 4, 1997, Pages 237-240

  Loh, Teck Peng ^a   Wang, Rui Bin ^a   Tan, Kee Leng ^a   Sim, Keng Yeow ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000343666     PISSN: 07921241     EISSN: 21910219     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. (a) Wang, R.-B.; Lim, C.-M.; Tan, C.-H.; Lim, B.-K.; Sim, K.-Y.; Loh, T.-P. Tetrahedron: Asymmetry. 1995, 6, 1825.
2. (b) Ho, D S.-C.; Sim, K.-Y.; Loh, T.-P. Synlett. 1996, 3, 263.
3. (c) Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry. 1996, 7, 1535.
4. (d) Loh, T.-P.; Ho, D S.-C.; Xu, K.-C.; Sim, K.-Y. Tetrahedron Lett, in press
5. (a) Loh, T.-P.; Pei, J.; Cao, G.-Q. Chem. Commun. 1996, 1819.
6. (b) Loh, T.-P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315.
7. (c) Loh, T.-P.; Li, X.-R. Chem. Commun. 1996, 1929.
8. Recent reviews on the dipeptide isosteres: (a) Spatola, A.F. Chem. Biochem. Amino Acids Pept. Proteins .1983, 7, 267.
9. (b) Jourwe, D. Janssen Chim. Acta . 1985, 3, 3.
10. Review on staline and its analogues: (c) Rich, D.H. In Proteinase Inhibitors; Barret, A.T.; Salvesen, G. Eds.; Elsevier: New York, 1986; p179.
11. (d) (3R, 4S)-Epistatine is a component of didemnins, a new class of cyto toxic cyclic dipeptides: Rinehart, K.L.; Gloer, Jr, J.B.; Huges, R.G.; Renis, Jr., H.E.; McGovren, E.B.; Swynenberg, E.B.; Stringfellow, D.A.; Kuentzel, S.L.; Li, L.H. Science. 1981, 212, 933.
12. (e) Jiang, T.L.; Liu, R.H.; Salmon, S.E. Cancer Chemother. Pharmacol. 1983, 11, 1.
13. (a) Reetz, M.T.; Drewes, M.W.; Schmitz, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 1141.
14. (b) Reetz, M.T. Pure & Appl. Chem. 1988, 60, 1607.
15. Reviews on chelation vs. non-chelation control: (c) Reetz, M.T. Angew. Chem. Int. Ed. Engl.. 1984, 23, 556.
16. (d) Reetz, M.T. Organotitanium reagents in organic Synthesis, Springer-Verlag, Berlin 1986, ch. 5.
17. (e) Gennari, C. Selectivities in Lewis Acid Promoted Reactions ed. Schinzer, D.; Kluwer Academic, Dordrecht, 1989, ch. 4.
18. The use of lanthanide triflates as Lewis acids for organic reactions in aqueous media has been well demonstrated. (a) Kobayashi, S.; Hachiya, I. J. Org. Chem., 1993, 58, 6958.
19. (b) Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis. 1993, 371.
20. (c) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Mitsuharu, A. Tetrahedron Lett. 1992, 33, 6815.
21. (d) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755.
22. (e) Mikami, K.; Terada, M.; Nakai, T. J. Org. Chem. 1991, 56, 5456.
23. (f) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry, 1991, 2, 993.
24. (g) Terada, M.; Gu, J.-H.; Deka, D.C.; Mikami, K.; Nakai, T. Chem. Lett. 1992, 29.
25. (h) Gu, J.-H.; Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1992, 33, 1465.
26. (i) Mikami, K.; Terada, M.; Nakai, T. J. Chem. Soc. Chem. Commun. 1993, 343.
27. (j) Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry, 1995, 6, 71.
28. (k) Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851.
29. Mikami, K.; Kaneko, M.; Loh, T.-P.; Terada, M.; Nakai, T. Tetrahedron Lett. 1990, 31, 3909.
30. Wu, W.L.; Yao, Z.-J.; Li, Y.-L.; Li, J.-C.; Xia, Y.; Wu, Y.-L. J. Org. Chem. 1995, 60, 3257.
31. 1H NMR after conversion to the Mosher ester (>99%ee), indicating that no racemization of the aminoaldehyde has occured. cf. Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org.Chem. 1969, 34, 2543.
32. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191.
33. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910.
34. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449.
35. (d) Einhorn, J.; Luche, J.-L. J. Organomet. Chem. 1987, 322, 177.
36. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697.
37. (f) Wilson, S.R.; Guazzaroni, M.E. J. Org. Chem. 1989, 54, 3087.
38. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279.
39. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674.
40. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714.
41. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500;
42. see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336.
43. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
44. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97.
45. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721.
46. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863.
47. (o) Paquette, L.A.; Lobben, P.C. J. Am. Chem. Soc. 1996, 118, 1917.
48. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
49. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
50. (b) Anh, N.; Top, T. Curr. Chem. 1980, 88, 145.