Stereoselective allyl amine synthesis via enantioselective addition of diethylzinc and sigmatropic rearrangement; synthesis of lentiginosine

Synlett

Volumn , Issue 7, 2003, Pages 1034-1036

  Ichikawa, Yoshiyasu ^a   Ito, Takashi ^a   Nishiyama, Taihei ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Amines; Asymmetric synthesis; Natural products; Rearrangements; Stereoselective

Indexed keywords

ALLYL COMPOUND; AMINE; CYANIC ACID; DIETHYLZINC; INOSINE DERIVATIVE; ISOCYANATE; LINTIGINOSINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038575875     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39314     Document Type: Article

References (29)

1. (a) Ichikawa, Y. Synlett 1991, 238.
2. (b) Ichikawa, Y.; Osada, M.; Ohtani, I.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1997, 1449.
3. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
4. Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791.
5. (a) Isolation: Pastuszak, I.; Molyneux, R. J.; James, L. F.; Elbein, A. D. Biochemistry 1990, 29, 188.
6. (b) For the synthetic works, see: Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymmetry 1993, 4, 1455.
7. (c) Gurjar, M. K.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871.
8. (d) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398.
9. (e) Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
10. (f) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
11. (g) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137.
12. (h) McCaig, A. E.; Meldrum, K. P.; Wightman, R. H. Tetrahedron 1998, 54, 9429.
13. (i) Ha, D.-C.; Yun, C.-S.; Lee, Y. J. Org. Chem. 2000, 65, 621.
14. (j) Yoda, H.; Katoh, H.; Ujihara, Y.; Takabe, K. Tetrahedron Lett. 2001, 42, 2509.
15. (k) Rasmussen, M. O.; Delair, P.; Greene, A. E. J. Org. Chem. 2001, 66, 5438.
16. (l) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056.
17. (m) Rabiczko, J.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 2002, 58, 1433.
18. (n) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
19. (o) Feng, Z.-X.; Zhou, W.-S. Tetrahedron Lett. 2003, 44, 497.
20. (p) Ayad, T.; Genisson, Y.; Baltas, M.; Gorrichon, L. Chem. Commun. 2003, 582.
21. (a) Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485.
22. (b) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
23. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337.
24. In this reaction, it should be noted that we can avoid matched-mismatched problems when R has stererogenic centers (Scheme 1), because asymmetric induction is carried out at the remote position where the effect of R group becomes negligible. In fact, synthesis of the diastereomer 23 was also achieved with Soai protocol simply employing (R)-DPMPM to furnish 23 with 93:7 diastereoselecctivity. Further transformation of 23 using similar procedures in Scheme 2 afforded the allyl carbamate 24 in good yield (Scheme 4). For the matched-mismatched problems, see the reference: Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1984, 24, 1.
25. The minor isomer produced in the step (8 → 9) was removed at this stage by recrystallisation of 14.
26. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
27. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 2039.
28. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1988, 4413.
29. 3): δ = 22.8, 23.8, 27.4, 52.4, 60.1, 68.3, 75.5, 82.8.