Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents: Synthesis and Application to Asymmetric Diels-Alder Reaction

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2634-2640

  Kitagawa, Osamu ^a   Izawa, Hirotaka ^a   Sato, Kiyonobu ^a   Dobashi, Akira ^a   Taguchi, Takeo ^a   Shiro, Motoo ^b  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000677060     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9721711     Document Type: Article

References (32)

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21. We have also found α-iodination reaction of unsaturated carboxaraides and N-allylic enamides derivatives through a similar iodine-mediated activating process. (a) Kitagawa, O.; Hanano, T.; Hirata, T.; Inoue, T.; Taguchi, T. Tetrahadron Lett 1992, 33, 1299. (b) Kitagawa, O.; Kikuchi, N.; Hanano, T.; Aoki, K.; Yamazaki, T.; Okada, M.; Taguchi, T. J. Org. Chem. 1995, 60, 7161.
22. We have also found α-iodination reaction of unsaturated carboxaraides and N-allylic enamides derivatives through a similar iodine-mediated activating process. (a) Kitagawa, O.; Hanano, T.; Hirata, T.; Inoue, T.; Taguchi, T. Tetrahadron Lett 1992, 33, 1299. (b) Kitagawa, O.; Kikuchi, N.; Hanano, T.; Aoki, K.; Yamazaki, T.; Okada, M.; Taguchi, T. J. Org. Chem. 1995, 60, 7161.
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24. Reviews in relation to asymmetric Diels-Alder reactions using a chiral auxiliary; (a) Paquette, L. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 455. (b) Helmchen, G.; Karge, R.; Weetman, J. Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: New York, 1986; Vol. 4, p 262. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Inc.: New York, 1991; Vol. 5, p 315. (d) Ishizuka, T.; Kunieda, T. Rev. Heteroat. Chem. 1996, 15, 227.
25. Reviews in relation to asymmetric Diels-Alder reactions using a chiral auxiliary; (a) Paquette, L. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 455. (b) Helmchen, G.; Karge, R.; Weetman, J. Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: New York, 1986; Vol. 4, p 262. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Inc.: New York, 1991; Vol. 5, p 315. (d) Ishizuka, T.; Kunieda, T. Rev. Heteroat. Chem. 1996, 15, 227.
26. Reviews in relation to asymmetric Diels-Alder reactions using a chiral auxiliary; (a) Paquette, L. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 455. (b) Helmchen, G.; Karge, R.; Weetman, J. Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: New York, 1986; Vol. 4, p 262. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Inc.: New York, 1991; Vol. 5, p 315. (d) Ishizuka, T.; Kunieda, T. Rev. Heteroat. Chem. 1996, 15, 227.
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30. The conformation of 1A was preexamined through MM and MD calculations using MM2 force field as implemented in MacroModel 4.5 (Department of Chemistry, Columbia University, New York), Molecular dynamics calculation in vacuo at 300 K was carried out with a path length of 100 ps and followed by minimizing random structures sampled after multiple 1 ps intervals. Final full geometry was then optimized by semiempirical PM3 calculation as implemented in SPARTAN 4.0 (Wave function Inc., California).
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32. 2AlCl, the reaction of (+)-2 with cyclohexadiene gave a complex mixture together with recovery of (+)-2.