Efficient asymmetric synthesis of Reissert compounds

Synlett

Volumn , Issue 3, 2003, Pages 337-340

  Sieck, Oxana ^a   Schaller, Steffen ^a   Grimme, Stefan ^b   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Amino acid fluorides; Asymmetric synthesis; Isoquinolines; Menthylchloroformate; Reissert compounds

Indexed keywords

ALKALOID DERIVATIVE; AMINO ACID DERIVATIVE; FLUORIDE; FORMIC ACID DERIVATIVE; HALIDE; ISOQUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; COLUMN CHROMATOGRAPHY; METHYLATION; STEREOCHEMISTRY;

EID: 0037288295     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37118     Document Type: Article

References (23)

1. (a) Sriven, E. F. V. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 165.
2. (b) Popp, F. D. In Advances in Heterocyclic Chemistry, Vol. 9; Katritzky, A. R., Ed.; Academic Press: London, 1968, 1.
3. (a) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327.
4. (b) Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
5. th International Congress of Heterocyclic Chemistry; ICHC: Yokohama, 2001,; Abstract number 30-PO-56: 203.
6. Surygina, O.; Ehwald, M.; Liebscher, J. Tetrahedron Lett. 2000, 41, 5479.
7. Itoh, T.; Nagata, K.; Miyazaki, M.; Kameoka, K.; Ohsawa, A. Tetrahedron 2001, 57, 8827.
8. Liebscher, J.; Surygina, O. presented at ICOS, Christchurch, New-Zealand, 2002.
9. 3: 361.1426. Found: 361.1420.
10. 20 25.8 (c 1, DMF)
11. (a) Comins, D. L.; Badawi, M. M. Heterocycles 1991, 32, 1869.
12. (b) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
13. (c) Comins, D. L.; Goehring, R. R.; Foseph, S. P.; O'Connor, S. J. Org. Chem. 1990, 55, 2574.
14. 2.
15. (a) Grimme, S. Chem. Phys. Lett. 2001, 339, 380.
16. (b) Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. J. Phys. Chem. A 2001, 105, 5356.
17. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.
18. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.
19. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.
20. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.
21. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.
22. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.
23. All quantum chemical calculations have been performed with the TURBOMOLE suite of programs: (a) TURBOMOLE (Vers. 5.5): A hlrichs, R.; Bär, M.; Baron, H.-P.; Bauemschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Hase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A. Schneider, U. Treutler, O.; von Amim, M.; Weigend, F.; Weis, P.; Weiss, H. Universität Karlsruhe 2002. The structures of 5 (Ph substiment replaced by a methyl group) and 12 have been fully optimised at the density functional (DFF) level employing the BP86 functional (b), a Gaussian AO basis of valence-double-zeta quality including polarisation functions (SVP) (c)and the RI-approximation for the two-electron integrals (d). The structures have been used in subsequent calculations of the frequency-dependent optical rotatory dispersion ([α]) at the sodium-D-line wavelength. These calculations have been performed in the framework of time-dependent DFT (e)as described in detail in (f). In the TDDFT approach the SVP basis sets augmented with diffuse basis functions (C, O: [1s1p1d], H: [1s1p]) have been used. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. (e) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283. (f) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454. (g)Grimme, S.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 361, 321.