Diastereoselective Ni(0)-catalyzed carbocyclization to chiral vinylic sulfoxide

Chemical Communications

Volumn , Issue 31, 2005, Pages 3992-3994

  Maezaki, Naoyoshi ^a   Sawamoto, Hiroaki ^a   Ishihara, Hiroyuki ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE; NICKEL; SULFOXIDE; VINYL DERIVATIVE;

ARTICLE; CARBOCYCLIZATION; CATALYSIS; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY;

EID: 23944515512     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506375b     Document Type: Article

References (28)

1. (a) I. Fernandez and N. Khiar, Chem. Rev., 2003, 103, 3651-3705;
2. (b) M. Narita, H. Urabe and F. Sato, Angew. Chem., Int. Ed., 2002, 41, 3671-3674;
3. (c) J. Adrio and J. C. Carretero, J. Am. Chem. Soc., 1999, 121, 7411-7412;
4. (d) J. M. Villar, A. Delgado, A. Llebaria, J. M. Moretó, E. Molins and C. Miravitlles, Tetrahedron, 1996, 52, 10525-10546.
5. For reviews, see: (a) J. Montgomery, Angew. Chem., Int. Ed., 2004, 43, 3890-3908;
6. (b) J. Montgomery, Acc. Chem. Res., 2000, 33, 467-473.
7. For selected recent examples, see: aldehyde-alkyne cyclization: (a) X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954;
8. aldehyde-allene cyclization: (b) K. K. D. Amarasinghe and J. Montgomery, J. Am. Chem. Soc., 2002, 124, 9366-9367;
9. aldehyde-diene cyclization: (c) Y. Sato, M. Takimoto and M. Mori, Chem. Pharm. Bull., 2000, 48, 1753-1760;
10. (d) Y. Sato, N. Saito and M. Mori, Tetrahedron, 1998, 54, 1153-1168;
11. unsaturated imide-alkyne cyclization: (e) Y. Ni, K. K. D. Amarasinghe, B. Ksebati and J. Montgomery, Org. Lett., 2003, 5, 3771-3773;
12. (f) R. S. Fornicola, K. Subburaj and J. Montgomery, Org. Lett., 2002, 4, 615-617;
13. unsaturated imide-allene cyclization: (g) M. V. Chevliakov and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 11139-11143;
14. bis-enone cyclization: (h) J. Seo, H. Fain, J.-B. Blanc and J. Montgomery, J. Org. Chem., 1999, 64, 6060-6065.
15. (a) M. C. Carreño, Chem. Rev., 1995, 95, 1717-1760;
16. (b) J. P. Marino, Pure Appl. Chem., 1993, 65, 667-674;
17. (c) A. J. Walker, Tetrahedron: Asymmetry, 1992, 3, 961-998;
18. (d) T. Koizumi, Phosphorus, Sulfur Silicon Relat. Elem., 1991, 58, 111-127.
19. N. Maezaki, H. Sawamoto, S. Yuyama, R. Yoshigami, T. Suzuki, M. Izumi, H. Ohishi and T. Tanaka, J. Org. Chem., 2004, 69, 6335-6340.
20. (a) J. Montgomery, E. Oblinger and A. V. Savchenko, J. Am. Chem. Soc., 1997, 119, 4911-4920;
21. (b) A. V. Savchenko and J. Montgomery, J. Org. Chem., 1996, 61, 1562-1563.
22. For recent review, see: (a) J. M. Seco, E. Quinoa and R. Riguera, Chem. Rev., 2004, 104, 17;
23. (b) T. Yabuuchi and T. Kusumi, J. Org. Chem., 2000, 65, 397-404.
24. (a) F. M. Dayrit and J. Schwartz, J. Am. Chem. Soc., 1981, 103, 4466-4473;
25. (b) F. M. Dayrit, D. E. Gladkowski and J. Schwartz, J. Am. Chem. Soc., 1980, 102, 3976-3978.
26. For mechanism of Ni-catalyzed carbocyclization, see: H. P. Hratchian, S. K. Chowdhury, V. M. Gutiérrez-García, K. K. D. Amarasinghe, M. J. Heeg, H. B. Schlegel and J. Montgomery, Organometallics, 2004, 23, 4636-4646,
27. Organometallics, 2004, 23, 5652 (Corrigendum).
28. L. F. Tietze, A. Schuffenhauer and P. R. Schreiner, J. Am. Chem. Soc., 1998, 120, 7952-7958.