An efficient synthesis of optically active five- and six-membered cyclic compounds with selectable stereo-controls by a Ti(II)-mediated cyclization of chiral secondary 2,7- and 2,8-enyn-1-ol derivatives

Tetrahedron Letters

Volumn 44, Issue 4, 2003, Pages 653-657

  Song, Yongcheng ^a   Takayama, Yuuki ^a   Okamoto, Sentaro ^a,b   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KANAGAWA UNIVERSITY   (Japan)

Author keywords

Chirality transfer; Cyclization; Leaving group; Olefinic geometry; Titanium

Indexed keywords

TITANIUM DERIVATIVE;

ARTICLE; CHIRALITY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

EID: 0037454988     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02695-3     Document Type: Article

References (27)

1. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
2. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
3. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
4. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
5. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
6. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
7. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
8. Reviews: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1; (b) Trost, B. M. Chem.-Eur. J. 1998, 4, 2405; (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; (d) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Recent examples: (e) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; (f) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490; (g) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714; (h) Adlington, R. M.; Baldwin, J. E.; Challis, G. L.; Cox, R. J.; Pritchard, G. J. Tetrahedron 2000, 56, 623.
9. Takayama Y., Gao Y., Sato F. Angew. Chem., Int. Ed. Engl. 36:1997;851.
10. Takayama Y., Okamoto S., Sato F. Tetrahedron Lett. 38:1997;8351.
11. Yamazaki T., Urabe H., Sato F. Tetrahedron Lett. 39:1998;7333.
12. Takayama Y., Okamoto S., Sato F. J. Am. Chem. Soc. 121:1999;3559.
13. Delas C., Urabe H., Sato F. Tetrahedron Lett. 42:2001;4147.
14. Song Y., Okamoto S., Sato F. Tetrahedron Lett. 43:2002;6511.
15. 4/2i-PrMgCl reagent: (a) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835; (b) Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759; (c) Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002; pp. 319-354.
16. 4/2i-PrMgCl reagent: (a) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835; (b) Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759; (c) Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002; pp. 319-354.
17. 4/2i-PrMgCl reagent: (a) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835; (b) Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759; (c) Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002; pp. 319-354.
18. Recent examples: (a) Togashi, K.; Terakado, M.; Miyazawa, M.; Yamamoto, K.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3333; (b) Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625; (c) Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415.
19. Recent examples: (a) Togashi, K.; Terakado, M.; Miyazawa, M.; Yamamoto, K.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3333; (b) Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625; (c) Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415.
20. Recent examples: (a) Togashi, K.; Terakado, M.; Miyazawa, M.; Yamamoto, K.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3333; (b) Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625; (c) Xie, X.; Lu, X. Tetrahedron Lett. 1999, 40, 8415.
21. 1H NMR analysis in the presence of 1 equiv. (R)-O-acetylmandelic acid. Ee values of the products (E)-/(Z)-10 were determined by chiral GLC analysis.
22. Authentic (S)-7 and (S)-18 were prepared as shown below:
23. Efficient Pd-catalyzed cyclization of optically active substrates was reported to afford chiral five- and six-membered cyclic compounds, which, however, always gave an (E)-alk-1-enyl side chain, see Refs. 4a, 4b and Oppolzer, W.; Birkinshaw, T. N.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Asymmetric cyclization providing (Z)-alk-1-enyl cyclic compounds, see Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219 and Takacs, J. M.; Anderson, L. G.; Creswell, M. W.; Takacs, B. E. Tetrahedron Lett. 1987, 28, 5627.
24. Efficient Pd-catalyzed cyclization of optically active substrates was reported to afford chiral five- and six-membered cyclic compounds, which, however, always gave an (E)-alk-1-enyl side chain, see Refs. 4a, 4b and Oppolzer, W.; Birkinshaw, T. N.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Asymmetric cyclization providing (Z)-alk-1-enyl cyclic compounds, see Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219 and Takacs, J. M.; Anderson, L. G.; Creswell, M. W.; Takacs, B. E. Tetrahedron Lett. 1987, 28, 5627.
25. Efficient Pd-catalyzed cyclization of optically active substrates was reported to afford chiral five- and six-membered cyclic compounds, which, however, always gave an (E)-alk-1-enyl side chain, see Refs. 4a, 4b and Oppolzer, W.; Birkinshaw, T. N.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 6995. Asymmetric cyclization providing (Z)-alk-1-enyl cyclic compounds, see Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219 and Takacs, J. M.; Anderson, L. G.; Creswell, M. W.; Takacs, B. E. Tetrahedron Lett. 1987, 28, 5627.
26. Kayser M.M., Chen G., Stewart J.D. J. Org. Chem. 63:1998;7103.
27. 2SiO group is unclear and the explanation must await further study.