Stereocontrolled cyclization of enynols and allenynols with (η2- propene)Ti(O-i-Pr)2. Important role of unprotected hydroxy group at a remote position

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7329-7332

  Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Cyclisation; Enynes; Stereoselection; Titanium and compounds

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032190783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01572-X     Document Type: Article

References (24)

1. [1] For reviews on group 4 transition metal-mediated cyclizations, see: (a) Buchwald SL, Nielsen RB. Chem. Rev. 1988;88:1047-1058.
2. (b) Negishi E. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;5:1163-1184.
3. (c) Negishi E, Takahashi T. Acc. Chem. Res. 1994;27:124-130.
4. (d) Sato F, Urabe H. In: Silverman GS, Rakita PE, editors. Handbook of Grignard Reagents. New York: Marcel Dekker, 1996:23-52.
5. [2] Hoveyda AH, Evans DA, Fu GC. Chem. Rev. 1993;93:1307-1370.
6. [3] Nishizawa M. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:159-182. Jones JB. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:183-209. Singh VK. Synthesis. 1992:605-617. Wallbaum S, Martens J. Tetrahedron:Asymmetry. 1992;3:1475-1504. Brown HC, Ramachandran PV. J. Organomet. Chem. 1995;500:1-19.
7. [3] Nishizawa M. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:159-182. Jones JB. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:183-209. Singh VK. Synthesis. 1992:605-617. Wallbaum S, Martens J. Tetrahedron:Asymmetry. 1992;3:1475-1504. Brown HC, Ramachandran PV. J. Organomet. Chem. 1995;500:1-19.
8. [3] Nishizawa M. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:159-182. Jones JB. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:183-209. Singh VK. Synthesis. 1992:605-617. Wallbaum S, Martens J. Tetrahedron:Asymmetry. 1992;3:1475-1504. Brown HC, Ramachandran PV. J. Organomet. Chem. 1995;500:1-19.
9. [3] Nishizawa M. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:159-182. Jones JB. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:183-209. Singh VK. Synthesis. 1992:605-617. Wallbaum S, Martens J. Tetrahedron:Asymmetry. 1992;3:1475-1504. Brown HC, Ramachandran PV. J. Organomet. Chem. 1995;500:1-19.
10. [3] Nishizawa M. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:159-182. Jones JB. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon Press, 1991;8:183-209. Singh VK. Synthesis. 1992:605-617. Wallbaum S, Martens J. Tetrahedron:Asymmetry. 1992;3:1475-1504. Brown HC, Ramachandran PV. J. Organomet. Chem. 1995;500:1-19.
11. [4] Hanessian S. Total Synthesis of Natural Products: The 'Chiron' Approach. Oxford: Pergamon Press, 1983.
12. [5] (a) RajanBabu TV, Nugent WA, Taber DF, Pagan PJ. J. Am. Chem. Soc. 1988;110:7128-7135.
13. (b) Nugent WA, Taber DF. J. Am. Chem. Soc. 1989;111:6435-6437.
14. (c) Agnel G, Owczarczyk Z, Negishi E. Tetrahedron Lett. 1992;33:1543-1546.
15. (d) Berk SC, Grossman RB, Buchwald SL. J. Am. Chem. Soc. 1994;116:8593-8601.
16. (e) Urabe H, Hata T, Sato F. Tetrahedron Lett. 1995;36:4261-4264.
17. (f) Pagenkopf BL, Lund EC, Livinghouse T. Tetrahedron. 1995;51:4421-4438.
18. (g) Hicks FA, Kablaoui NM, Buchwald SL. J. Am. Chem. Soc. 1996:118:9450-9451.
19. (h) Urabe H, Suzuki K, Sato F. J. Am. Chem. Soc. 1997;119:10014-10027.
20. [6] (a) Urabe H, Takeda T, Sato F. Tetrahedron Lett. 1996:37:1253-1256.
21. (b) Urabe H, Sato F. J. Org. Chem. 1996;61:6756-6757.
22. (c) Suzuki K, Urabe H, Sato F. J. Am. Chem. Soc. 1996;118:8729-8730.
23. (d) Hideura D, Urabe H, Sato F. Chem. Commun. 1998:271-272.
24. [7] Urabe H; Takeda T; Hideura D, Sato F. J. Am. Chem. Soc. 1997;119:11295-11305.