Titanium(II)-mediated asymmetric intramolecular cyclization of 2,7- and 2,8-enynyl chiral acetals. Synthetic equivalent of stoichiometric intramolecular asymmetric metallo-ene reaction [16]

Journal of the American Chemical Society

Volumn 121, Issue 14, 1999, Pages 3559-3560

  Takayama, Yuuki ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE; CYCLOPENTANE; TITANIUM;

CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; LETTER; STOICHIOMETRY; SYNTHESIS;

EID: 0033553152     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990021x     Document Type: Letter

References (23)

1. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 29-61. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863-871 and references therein.
2. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 29-61. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863-871 and references therein.
3. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 29-61. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863-871 and references therein.
4. (a) The preparation of optically active compounds containing an intrinsic stereogenic center of the optically active starting substrates through highly diastereoselective metallo-ene reaction has been reported; see ref 1.
5. (b) Catalytic asymmetric intramolecullar metallo-ene reactions induced by chiral ligands on the metal showing low to moderate enantioselectivity have been reported recently, see: Oppolzer, W.; Kuo D. L.; Hutzinger M. W.; Léger, R.; Durand J.-O.; Leslie C. Tetrahedron Lett. 1997, 38, 6213-6216.
6. 2Zr-mediated reaction; see, Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
7. 2Zr-mediated reaction; see, Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
8. 2Zr-mediated reaction; see, Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
9. 2Zr-mediated reaction; see, Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
10. 2Zr-mediated reaction; see, Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
11. 2Zr-mediated reaction; see, Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
12. 1H NMR analysis using a chiral shift reagent, tris[3-(heptafluropropylhydroxymethylene)-(+)-comphorato]europium(III); for 12, GC analysis after changing to 6 by dehalogenation with t-BuLi; for 15 and 17, GC analysis after converting to the corresponding dimethylacetal.
13. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590. Alexakis, A.; Mangeney P. Tetrahedron: Asymmetry 1990, 1, 477-511. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265-1276 and references therein.
14. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590. Alexakis, A.; Mangeney P. Tetrahedron: Asymmetry 1990, 1, 477-511. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265-1276 and references therein.
15. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590. Alexakis, A.; Mangeney P. Tetrahedron: Asymmetry 1990, 1, 477-511. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265-1276 and references therein.
16. Hashimoto, S.; Miyazaki, Y.; Ikegami, S. Synth. Commun. 1992, 22, 2717-2722. Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 7171-7172.
17. Hashimoto, S.; Miyazaki, Y.; Ikegami, S. Synth. Commun. 1992, 22, 2717-2722. Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 7171-7172.
18. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; VoL 5, pp 1037-1064. Recently, asymmetric Pauson-Khand reaction providing bicyclo[3,3,0]oct-1-en-3-ones has met with great success, see:
19. Castro, J.; Sorensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericás, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389. Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3521-3524. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688-11689.
20. Castro, J.; Sorensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericás, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389. Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3521-3524. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688-11689.
21. Castro, J.; Sorensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericás, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389. Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3521-3524. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688-11689.
22. Absolute configuration of 15 was speculated on the basis of analogy for the conversion 4 to 5.
23. Absolute configuration of Z-17 was established by correlation to known (S)-2-ethylcyclohexanone (see Supporting Information). Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081-3087.