Addition of Organolithiums to the (R)-O-(1-Phenylbutyl)hydroxylamine (ROPHy) Oxime of Cinnamaldehyde. Asymmetric Synthesis of α-Aminoacids

Synlett

Volumn 1997, Issue 6, 1997, Pages 659-660

  Moody, Christopher J ^c   Lightfoot, Andrew P ^a   Gallagher, Peter T ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

^c UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002900313     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3252     Document Type: Article

References (25)

1. For reviews, see: Williams, R. M. Synthesis of optically active α-amino acids; Pergamon: Oxford, 1989; Vol. 7; Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; North, M. Cont. Org. Synth. 1995, 2, 269-287; North, M. Cont. Org. Synth. 1996, 3, 323-343.
2. For reviews, see: Williams, R. M. Synthesis of optically active α-amino acids; Pergamon: Oxford, 1989; Vol. 7; Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; North, M. Cont. Org. Synth. 1995, 2, 269-287; North, M. Cont. Org. Synth. 1996, 3, 323-343.
3. For reviews, see: Williams, R. M. Synthesis of optically active α-amino acids; Pergamon: Oxford, 1989; Vol. 7; Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; North, M. Cont. Org. Synth. 1995, 2, 269-287; North, M. Cont. Org. Synth. 1996, 3, 323-343.
4. For reviews, see: Williams, R. M. Synthesis of optically active α-amino acids; Pergamon: Oxford, 1989; Vol. 7; Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; North, M. Cont. Org. Synth. 1995, 2, 269-287; North, M. Cont. Org. Synth. 1996, 3, 323-343.
5. For recent examples, see: Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911; Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. Amino Acids 1996, 11, 259-268; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Maneiro, E.; Miranda, J. I.; Urchegui, R. Chem. Comm. 1996, 161-162; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Urchegui, R.; Görls, H. Chem. Comm. 1996, 1269-1270; Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175-3178.
6. For recent examples, see: Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911; Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. Amino Acids 1996, 11, 259-268; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Maneiro, E.; Miranda, J. I.; Urchegui, R. Chem. Comm. 1996, 161-162; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Urchegui, R.; Görls, H. Chem. Comm. 1996, 1269-1270; Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175-3178.
7. For recent examples, see: Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911; Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. Amino Acids 1996, 11, 259-268; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Maneiro, E.; Miranda, J. I.; Urchegui, R. Chem. Comm. 1996, 161-162; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Urchegui, R.; Görls, H. Chem. Comm. 1996, 1269-1270; Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175-3178.
8. For recent examples, see: Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911; Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. Amino Acids 1996, 11, 259-268; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Maneiro, E.; Miranda, J. I.; Urchegui, R. Chem. Comm. 1996, 161-162; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Urchegui, R.; Görls, H. Chem. Comm. 1996, 1269-1270; Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175-3178.
9. For recent examples, see: Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911; Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. Amino Acids 1996, 11, 259-268; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Maneiro, E.; Miranda, J. I.; Urchegui, R. Chem. Comm. 1996, 161-162; Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Urchegui, R.; Görls, H. Chem. Comm. 1996, 1269-1270; Pandey, G.; Reddy, P. Y.; Das, P. Tetrahedron Lett. 1996, 37, 3175-3178.
10. For recent examples, see: Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440-441; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273-5276; Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 8997-9000; Badorrey, R.; Cativiela, C.; Diaz -de-Villegas, M. D.; Galvez, J. A. Tetrahedron 1997, 53, 1411-1416.
11. For recent examples, see: Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440-441; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273-5276; Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 8997-9000; Badorrey, R.; Cativiela, C.; Diaz -de-Villegas, M. D.; Galvez, J. A. Tetrahedron 1997, 53, 1411-1416.
12. For recent examples, see: Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440-441; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273-5276; Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 8997-9000; Badorrey, R.; Cativiela, C.; Diaz -de-Villegas, M. D.; Galvez, J. A. Tetrahedron 1997, 53, 1411-1416.
13. For recent examples, see: Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440-441; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273-5276; Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 8997-9000; Badorrey, R.; Cativiela, C.; Diaz -de-Villegas, M. D.; Galvez, J. A. Tetrahedron 1997, 53, 1411-1416.
14. Gallagher, P. T.; Lightfoot, A. P.; Moody, C. J.; Slawin, A. M. Z. Synlett 1995, 445-446; Brown, D. S.; Gallagher, P. T.; Lightfoot, A. P.; Moody, C. J.; Slawin, A. M. Z.; Swann, E. Tetrahedron 1995, 51, 11473-11488.
15. Gallagher, P. T.; Lightfoot, A. P.; Moody, C. J.; Slawin, A. M. Z. Synlett 1995, 445-446; Brown, D. S.; Gallagher, P. T.; Lightfoot, A. P.; Moody, C. J.; Slawin, A. M. Z.; Swann, E. Tetrahedron 1995, 51, 11473-11488.
16. P. T. Gallagher, J. C. A. Hunt, A. P. Lightfoot, and C. J. Moody, submitted for publication.
17. Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. J. Org. Chem. 1997, 62, 746-748.
18. 3) 155.8, 143.1, 136.5, 132.4, 128.6, 128.2, 128.1, 127.2, 126.7, 126.4, 85.3, 38.7, 18.4, 14.0, 10.4.
19. General procedure: The cinnamaldoxime 1 (0.9 g, 3.22 mmol) in toluene (16 mL) was cooled to -78°C under nitrogen and boron trifluoride etherate (1.2 mL, 9.7 mmol) was added. The solution was stirred for 15 min; after this time the organometallic reagent (9.7 mmol) was added dropwise over 15 min, and the resulting clear solution was stirred for a further 30 min. Aqueous work-up and chromatography (5% ether / light petroleum) gave the hydroxylamine 2.
20. Enders, D.; Kempen, H. Synlett 1994, 969-971.
21. 4), filtered and evaporated. Column chromatography of the residue on silica gel (ether-light petroleum 1:6) gave the N-Cbz-amine 3.
22. 2O (0.03 mmol) was added and the solution heated at 50°C for 24 h. Aqueous work-up gave the N-Cbz-aminoacid 4.
23. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280-1285.
24. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450-1456.
25. Chiracel OD column, 39% isopropanol in hexane eluent, 1 mL/min flow rate.