N-Cbz-Trifluoropyruvaldehyde N,S-ketal: Absolute stereochemistry and addition of Grignard reagents. Highly stereoselective entry to trifluoro analogues of Ephedra alkaloids

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1847-1850

  Volonterio, Alessandro ^a   Bravo, Pierfrancesco ^a   Capelli, Silvia ^a   Meille, Stefano V ^a   Zanda, Matteo ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; REAGENT;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; FLUORINATION; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0031562383     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00209-8     Document Type: Article

References (25)

1. 1. Resnati, G. Tetrahedron 1993, 49, 9385-9445. Filler, R.; Kobayashi, Y.; Yagupolskii, L.M. Biomedical Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1993.
2. 1. Resnati, G. Tetrahedron 1993, 49, 9385-9445. Filler, R.; Kobayashi, Y.; Yagupolskii, L.M. Biomedical Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1993.
3. 2. Banks, R. E.; Tatlow, J. C.; Smart, B. E. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
4. 3. Bravo, P.; Crucianelli, M.; Fronza, G.; Zanda, M. Synlett 1996, 249-251. Full paper in preparation.
5. 4. (a) For N-monoprotected α-amino aldehydes see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. Devant, R. M.; Radunz, H.-E. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme Verlag: Stuttgart, 1995; Vol. E21b, p. 1151.
6. 4. (a) For N-monoprotected α-amino aldehydes see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164. Devant, R. M.; Radunz, H.-E. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme Verlag: Stuttgart, 1995; Vol. E21b, p. 1151.
7. (b) For chiral α-trifluoromethylated aldehydes: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199-208.
8. (c) For α-sulfenyl aldehydes: Eames, J.; de las Heras, M. A.; Warren, S. Tetrahedron Lett. 1996, 37, 4077-4080. Eames, J.; Jones, R. V. H.; Warren, S. Ibid. 1996, 37, 4823-4826. Sato, T.; Otera, J. Synlett 1995, 351-352.
9. (c) For α-sulfenyl aldehydes: Eames, J.; de las Heras, M. A.; Warren, S. Tetrahedron Lett. 1996, 37, 4077-4080. Eames, J.; Jones, R. V. H.; Warren, S. Ibid. 1996, 37, 4823-4826. Sato, T.; Otera, J. Synlett 1995, 351-352.
10. (c) For α-sulfenyl aldehydes: Eames, J.; de las Heras, M. A.; Warren, S. Tetrahedron Lett. 1996, 37, 4077-4080. Eames, J.; Jones, R. V. H.; Warren, S. Ibid. 1996, 37, 4823-4826. Sato, T.; Otera, J. Synlett 1995, 351-352.
11. 3. (equation presented)
12. 6. Syn and anti descriptors refer to the relative position of the amino and the hydroxy groups with respect to the molecular carbon backbone.
13. 3 group, the latter of which has been proposed to be of similar size as the isopropyl group (see ref. 4b), is not surprising. In fact, arylthio ligands have been reported to be remarkably "larger" than the isopropyl group. See for example: Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. J. Org. Chem. 1992, 57, 456-461.
14. 3 group, the latter of which has been proposed to be of similar size as the isopropyl group (see ref. 4b), is not surprising. In fact, arylthio ligands have been reported to be remarkably "larger" than the isopropyl group. See for example: Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. J. Org. Chem. 1992, 57, 456-461.
15. 3 group, the latter of which has been proposed to be of similar size as the isopropyl group (see ref. 4b), is not surprising. In fact, arylthio ligands have been reported to be remarkably "larger" than the isopropyl group. See for example: Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. J. Org. Chem. 1992, 57, 456-461.
16. 3 group, the latter of which has been proposed to be of similar size as the isopropyl group (see ref. 4b), is not surprising. In fact, arylthio ligands have been reported to be remarkably "larger" than the isopropyl group. See for example: Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. J. Org. Chem. 1992, 57, 456-461.
17. 8. Helmchen, G.; Nill, G.; Flockerzi, D.; Schuhle W.; Youssef, M. S. K. Angew. Chem. Int. Ed. Engl. 1979, 18, 62-63. Bravo, P.; Ganazzoli, F.; Resnati, G.; De Munari, S.; Albinati, A. J. Chem. Res. 1988, (S) 216-217, (M) 1701-1739.
18. 8. Helmchen, G.; Nill, G.; Flockerzi, D.; Schuhle W.; Youssef, M. S. K. Angew. Chem. Int. Ed. Engl. 1979, 18, 62-63. Bravo, P.; Ganazzoli, F.; Resnati, G.; De Munari, S.; Albinati, A. J. Chem. Res. 1988, (S) 216-217, (M) 1701-1739.
19. 2 using SHELXL93 (Sheldrick, G.M. 1993, SHELXL93, Program for the Refinement of Crystal structures, University of Göttingen, Germany). Non-hydrogen atoms were refined anisotropically. The amide hydrogen has been located by difference-Fourier technique and refined while the others have been included at calculated positions and refined with group temperature factors. Molecular dimensions fall in the expected ranges.
20. 2 using SHELXL93 (Sheldrick, G.M. 1993, SHELXL93, Program for the Refinement of Crystal structures, University of Göttingen, Germany). Non-hydrogen atoms were refined anisotropically. The amide hydrogen has been located by difference-Fourier technique and refined while the others have been included at calculated positions and refined with group temperature factors. Molecular dimensions fall in the expected ranges.
21. 10. Johnson, C.K. 1976, ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee.
22. 11. Marti, R. E.; Heinzer, J.; Seebach, D. Liebigs Ann. 1995, 1193-1215. Beck, A. K.; Seebach, D. Chem. Ber. 1991, 124, 2897-2911.
23. 11. Marti, R. E.; Heinzer, J.; Seebach, D. Liebigs Ann. 1995, 1193-1215. Beck, A. K.; Seebach, D. Chem. Ber. 1991, 124, 2897-2911.
24. 12. Ogura, K.; Yoshimura, I.; Katoh, N.; Tsuchihashi, G. Chem. Lett. 1975, 803-804.
25. 3), has been recently synthesized in these laboratories by a completely different strategy. The related manuscript is in preparation.