Efficient synthesis of 7-, 8- and 9-membered cyclic allyltitanium compounds and their stereoselective addition reaction with aldehydes and imines

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2867-2870

  Hikichi, Shinichi ^a   Gao, Yuan ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030951974     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00484-X     Document Type: Article

References (12)

1. (a) Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881-3882;
2. (b) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136-8137.
3. 3-cycloallyl) and their reactions with electrophiles have been reported, see: Kobayashi, Y.; Umeyama, K.; Sato, F. J. C. S., Chem. Commun. 1984, 621-623; Szymoniak, J.; Pagneux, S.; Felix, D.; Moïse, C. Synlett 1996, 46-48 and references cited therein.
4. 3-cycloallyl) and their reactions with electrophiles have been reported, see: Kobayashi, Y.; Umeyama, K.; Sato, F. J. C. S., Chem. Commun. 1984, 621-623; Szymoniak, J.; Pagneux, S.; Felix, D.; Moïse, C. Synlett 1996, 46-48 and references cited therein.
5. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.
6. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.
7. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 5.
8. 4 and concentrated to an oil, which was chromatographed on silica gel to afford 1-(2-cycloocten-1-yl)propan-1-ol (0.117 g, 85% yield).
9. Fujita, K.; and Schlosser, M. Helv. Chim. Acta 1982, 65, 1258-1263.
10. 13C NMR spectra with syn-4 prepared as follows: formula represented
11. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin/Heidelberg, 1986.
12. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778.