1,5-Asymmetric Induction in Squarate Cascades. Conformational Control of Helicity by Chiral Amino Substituants during Conrotatory Octatetraene Cyclization Prior to β-Elimination

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 2022-2030

  Paquette, Leo A ^a   Tae, Jinsung ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001371532     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9722921     Document Type: Article

References (24)

1. (a) Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189.
2. (b) Paquette, L. A.; Morwick, T. J. Am. Chem. Soc. 1995, 117, 1451.
3. (c) Paquette, L. A.; Doyon, J. J. Am. Chem. Soc. 1995, 117, 6799.
4. (d) Paquette, L. A.; Morwick, T. J. Am. Chem. Soc. 1997, 119, 1230.
5. (e) Paquette, L. A.; Doyon, J. J. Org. Chem. 1997, 62, 1723.
6. Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1996, 61, 146.
7. Paquette, L. A.; Morwick, T. M.; Negri, J. T.; Rogers, R. D. Tetrahedron 1996, 52, 3075.
8. Paquette, L. A.; Kuo, L. H.; Doyon, J. Tetrahedron 1996, 52, 11625.
9. Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038.
10. Paquette, L. A.; Kuo, L. H.; Tae, J. J. Org. Chem. 1998, 63, 2010 (preceding paper in this issue).
11. Paquette, L. A.; Hamme, A. T., II.; Kuo, L. H.; Doyon, J.; Kreuzholz, R. J. Am. Chem. Soc. 1997, 119, 1242.
12. Paquette, L. A., Kuo, L. H.; Hamme, A. T., II; Kreuzholz, R.; Doyon, J. J. Org. Chem. 1997, 62, 1730.
13. Procter, G. Asymmetric Synthesis; Oxford University Press: Oxford, England, 1996.
14. For an analysis of conformational transmission of chirality in the specific case of a 1,4-asymmetric induction process, consult: Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826.
15. The primary amines required for the preparation of 11, 12, 16, 17, and 18 as well as the secondary amine precursor to 14 were purchased from the Aldrich Chemical Co. endo-Bornylamine was prepared from D-camphor (Forster, M. O. J. Chem. Soc. 1898, 73, 386), (S)-(+)-2-(methoxymethyl)pyrrolidine from (S)-proline (Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173), and (2S,5S)-2,5-dimethylpyrrolidine from L-alanine (Yamazaki, T.; Gimi, R.; Welch, J. T. Synlett 1991, 573).
16. The primary amines required for the preparation of 11, 12, 16, 17, and 18 as well as the secondary amine precursor to 14 were purchased from the Aldrich Chemical Co. endo-Bornylamine was prepared from D-camphor (Forster, M. O. J. Chem. Soc. 1898, 73, 386), (S)-(+)-2-(methoxymethyl)pyrrolidine from (S)-proline (Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173), and (2S,5S)-2,5-dimethylpyrrolidine from L-alanine (Yamazaki, T.; Gimi, R.; Welch, J. T. Synlett 1991, 573).
17. The primary amines required for the preparation of 11, 12, 16, 17, and 18 as well as the secondary amine precursor to 14 were purchased from the Aldrich Chemical Co. endo-Bornylamine was prepared from D-camphor (Forster, M. O. J. Chem. Soc. 1898, 73, 386), (S)-(+)-2-(methoxymethyl)pyrrolidine from (S)-proline (Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173), and (2S,5S)-2,5-dimethylpyrrolidine from L-alanine (Yamazaki, T.; Gimi, R.; Welch, J. T. Synlett 1991, 573).
18. (a) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929.
19. (b) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
20. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
21. Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
22. Danehey, C. T., Jr.; Grady, G. L.; Bonneau, P. R.; Bushweller, C. H. J. Am. Chem. Soc. 1988, 110, 7269.
23. (a) Berson, J. A.; Dervan, P. B. J. Am. Chem. Soc. 1972, 94, 7597.
24. (b) Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201.