The olefinic aldol reaction. Intramolecular cyclization forming five- and six-membered rings

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2157-2158

  Nakamura, Eiichi ^a   Sakata, Go ^a   Kubota, Katsumi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE; CYCLOPENTANE; HYDRAZONE DERIVATIVE; LACTAM;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY;

EID: 0032499077     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00145-2     Document Type: Article

References (11)

1. 1 Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792-793; Kubota, K.; Nakamura, E. Angew. Chem. Int. Ed. Engl., 1997, 36, 2491-2493; Nakamura, E.; Kubota, K. Tetrahedron Lett. 1997, 38, 7099-7102.
2. 1 Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792-793; Kubota, K.; Nakamura, E. Angew. Chem. Int. Ed. Engl., 1997, 36, 2491-2493; Nakamura, E.; Kubota, K. Tetrahedron Lett. 1997, 38, 7099-7102.
3. 1 Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792-793; Kubota, K.; Nakamura, E. Angew. Chem. Int. Ed. Engl., 1997, 36, 2491-2493; Nakamura, E.; Kubota, K. Tetrahedron Lett. 1997, 38, 7099-7102.
4. 2 Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458
5. 3 Karoyan, P.; Chassaing, G. Tetrahedron Lett. 1997, 38, 85-88; Lorthiois, E.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 89-92.
6. 3 Karoyan, P.; Chassaing, G. Tetrahedron Lett. 1997, 38, 85-88; Lorthiois, E.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 89-92.
7. 2O in pentane) afforded the 5-exo cyclization product in entry 1 (7.10 g, 90%, as a yellow oil) as an 88:12 mixture of cis- and trans-isomers as determined by capillary GC analysis (HR-1).
8. 5 Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056-8066. See also: Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
9. 5 Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056-8066. See also: Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
10. 6 Conia, J. M.: Perchec, P. Le. Synthesis 1975, 1-19.
11. 7 We thank Dr. M. Nakamura and H. Isobe for discussions. This work was supported by Grant-in-Aid for Scientific Research on Priority Areas (No. 283, "Innovative Synthetic Reactions©) from Monbusho.