Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids

Journal of the American Chemical Society

Volumn 127, Issue 4, 2005, Pages 1066-1067

  Workman, James A ^a   Garrido, Neil P ^a   Sançon, Julien ^a   Roberts, Edward ^b,c   Wessel, Hans Peter ^b   Sweeney, J B ^a  

^a UNIVERSITY OF READING   (United Kingdom)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

^c Kemia Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALLYL COMPOUNDS; ALLYLGLYCINE; GLYCINE; QUATERNARY AMMONIUM COMPOUNDS;

EID: 13644259133     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043768i     Document Type: Article

References (25)

1. For reviews of the area, see: (a) Markó, I. E. Compr. Org. Synth. 1991, 3, 913. (b) Nitrogen, Oxygen and Sulfur Ylide Chemistry; Clark, J. S., Ed.; Oxford University Press: Oxford; 2002. (c) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley & Sons: New York, 1998.
2. For reviews of the area, see: (a) Markó, I. E. Compr. Org. Synth. 1991, 3, 913. (b) Nitrogen, Oxygen and Sulfur Ylide Chemistry; Clark, J. S., Ed.; Oxford University Press: Oxford; 2002. (c) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley & Sons: New York, 1998.
3. For reviews of the area, see: (a) Markó, I. E. Compr. Org. Synth. 1991, 3, 913. (b) Nitrogen, Oxygen and Sulfur Ylide Chemistry; Clark, J. S., Ed.; Oxford University Press: Oxford; 2002. (c) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley & Sons: New York, 1998.
4. For original reports of onium ylid rearrangements, see: Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. Blackburn, G. M.; Ollis, W. D.; Smith, C.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1968, 186. Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1968, 537, 538.
5. For original reports of onium ylid rearrangements, see: Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. Blackburn, G. M.; Ollis, W. D.; Smith, C.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1968, 186. Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1968, 537, 538.
6. For original reports of onium ylid rearrangements, see: Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. Blackburn, G. M.; Ollis, W. D.; Smith, C.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1968, 186. Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1968, 537, 538.
7. Doyle, M. P.; Tamblyn, W. H.; Bagheri, V. J. Org. Chem. 1981, 46, 5094.
8. See, for instance: Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1997, 2951. Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072 and references therein.
9. See, for instance: Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1997, 2951. Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072 and references therein.
10. Burns, B.; Coates, B.; Neeson, S.; Stevenson, P. J. Tetrahedron Lett. 1990, 31, 4351. Neeson, S. J.; Stevenson, P. J. Tetrahedron Lett. 1988, 29, 3993.
11. Burns, B.; Coates, B.; Neeson, S.; Stevenson, P. J. Tetrahedron Lett. 1990, 31, 4351. Neeson, S. J.; Stevenson, P. J. Tetrahedron Lett. 1988, 29, 3993.
12. Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113.
13. For reports of syntheses and the significance of allyl glycines, see: Walsh C. Tetrahedron 1982, 38, 871. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Bioulac, B.; Benazzouz, A.; Burbaud, P.; Gross, C. Neurosci. Lett. 1997, 226, 21. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488. Gurjar M. K.; Talukdar A. Synthesis 2002, 315 and references therein.
14. For reports of syntheses and the significance of allyl glycines, see: Walsh C. Tetrahedron 1982, 38, 871. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Bioulac, B.; Benazzouz, A.; Burbaud, P.; Gross, C. Neurosci. Lett. 1997, 226, 21. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488. Gurjar M. K.; Talukdar A. Synthesis 2002, 315 and references therein.
15. For reports of syntheses and the significance of allyl glycines, see: Walsh C. Tetrahedron 1982, 38, 871. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Bioulac, B.; Benazzouz, A.; Burbaud, P.; Gross, C. Neurosci. Lett. 1997, 226, 21. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488. Gurjar M. K.; Talukdar A. Synthesis 2002, 315 and references therein.
16. For reports of syntheses and the significance of allyl glycines, see: Walsh C. Tetrahedron 1982, 38, 871. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Bioulac, B.; Benazzouz, A.; Burbaud, P.; Gross, C. Neurosci. Lett. 1997, 226, 21. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488. Gurjar M. K.; Talukdar A. Synthesis 2002, 315 and references therein.
17. For reports of syntheses and the significance of allyl glycines, see: Walsh C. Tetrahedron 1982, 38, 871. Duthaler, R. O. Tetrahedron 1994, 50, 1539. Bioulac, B.; Benazzouz, A.; Burbaud, P.; Gross, C. Neurosci. Lett. 1997, 226, 21. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488. Gurjar M. K.; Talukdar A. Synthesis 2002, 315 and references therein.
18. For a recent report of a Lewis-acid-mediated rearrangement, see: Blid, J.; Brandt, P.; Somfai, P. J. Org. Chem. 2004, 69, 3043.
19. Stereochemistry confirmed by X-ray analysis.
20. For a previous report of [2,3]-rearrangements of triallylammonium salts, see: Arbore, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236.
21. Garro-Helion, F.; Merzouk, A.; Guibé, F. J. Org. Chem. 1993, 58, 6109.
22. Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta 1992, 75, 1965.
23. There is significant variation between the values reported for the specific rotation of the antipodes of allylglycine: the N-Cbz-OMe derivative of our material was shown to be ≥95% (R)-configured by HPLC.
24. (a) Myers, A. G.; Gleason, J. L. Org. Synth. 1999, 76, 57.
25. (b) Broxterman, Q. B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. J. Org. Chem. 1992, 57, 6286.