Enantioselective α-Silyl Amino Acid Synthesis by Reverse-Aza-Brook Rearrangement

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4677-4679

  Liu, Guodong ^a   Sieburth, Scott McN ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYLAMINE DERIVATIVE; AMINO ACID DERIVATIVE; SILANE DERIVATIVE; TRIFLUOROACETIC ACID; TRIPEPTIDE;

ARTICLE; ENANTIOMER; ENANTIOSELECTIVITY; OXIDATION; STANDARDIZATION; SYNTHESIS;

ALLYLAMINE; AMINO ACIDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEPTIDES; SILANES; STEREOISOMERISM; TRIFLUOROACETIC ACID;

EID: 0347411066     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0358713     Document Type: Article

References (26)

1. Mendel, D.; Ellman, J. A.; Chang, Z.; Veenstra, D. L.; Kollman, P. A.; Schultz, P. G. Science (Washington, D.C.) 1992, 256, 1798-1802. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. Horng, J.-C.; Raleigh, D. P. J. Am. Chem. Soc. 2003, 125, 9286-9287.
2. Mendel, D.; Ellman, J. A.; Chang, Z.; Veenstra, D. L.; Kollman, P. A.; Schultz, P. G. Science (Washington, D.C.) 1992, 256, 1798-1802. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. Horng, J.-C.; Raleigh, D. P. J. Am. Chem. Soc. 2003, 125, 9286-9287.
3. Mendel, D.; Ellman, J. A.; Chang, Z.; Veenstra, D. L.; Kollman, P. A.; Schultz, P. G. Science (Washington, D.C.) 1992, 256, 1798-1802. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. Horng, J.-C.; Raleigh, D. P. J. Am. Chem. Soc. 2003, 125, 9286-9287.
4. Mendel, D.; Ellman, J. A.; Chang, Z.; Veenstra, D. L.; Kollman, P. A.; Schultz, P. G. Science (Washington, D.C.) 1992, 256, 1798-1802. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. Horng, J.-C.; Raleigh, D. P. J. Am. Chem. Soc. 2003, 125, 9286-9287.
5. Adessi, C.; Soto, C. Curr. Med. Chem. 2002, 9, 963-978.
6. Mori, A.; Abe, H.; Inoue, S. Appl. Organomet. Chem. 1995, 9, 189-197.
7. (a) Birkofer, L.; Ritter, A. Angew. Chem. 1956, 68, 461-462.
8. (b) Birkofer, L.; Ritter, A. Liebigs Ann. Chem. 1958, 612, 22-33.
9. (c) See also: Tacke, R.; Handmann, V. I. Organometallics 2002, 21, 2619-2626 and references therein.
10. For examples, see: Weidmann, B. Chimia 1992, 46, 312-313. Wienand, A.; Ehrhardt, C.; Metternich, R.; Tapparelli, C. Bioorg. Med. Chem. 1999, 7, 1295-1307. Tacke, R.; Merget, M.; Bertermann, R.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497.
11. For examples, see: Weidmann, B. Chimia 1992, 46, 312-313. Wienand, A.; Ehrhardt, C.; Metternich, R.; Tapparelli, C. Bioorg. Med. Chem. 1999, 7, 1295-1307. Tacke, R.; Merget, M.; Bertermann, R.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497.
12. For examples, see: Weidmann, B. Chimia 1992, 46, 312-313. Wienand, A.; Ehrhardt, C.; Metternich, R.; Tapparelli, C. Bioorg. Med. Chem. 1999, 7, 1295-1307. Tacke, R.; Merget, M.; Bertermann, R.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497.
13. Bolm, C.; Kasyan, A.; Drauz, K.; Günther, K.; Raabe, G. Angew. Chem., Int. Ed. 2000, 39, 2288-2290.
14. Chen, J.-X.; Tunge, J. A.; Norton, J. R. J. Org. Chem. 2002, 67, 4366-4369.
15. Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547-1550. Sun, H.; Moeller, K. D. Org. Lett. 2003, 5, 3189-3192.
16. Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547-1550. Sun, H.; Moeller, K. D. Org. Lett. 2003, 5, 3189-3192.
17. Sieburth, S. McN.; Somers, J. J.; O'Hare, H. K. Tetrahedron 1996, 52, 5669-5682.
18. Sieburth, S. McN.; O'Hare, H. K.; Xu, J.; Chen, Y.; Liu, G. Org. Lett. 2003, 5, 1859-1861.
19. The examples of oxidative allylsilane cleavage to α-silyl aldehydes that we are aware of are those of Landais: Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 23, 4037-4053. Landais, Y.; Zekri, E. Tetrahedron Lett. 2001, 42, 6547-6551.
20. The examples of oxidative allylsilane cleavage to α-silyl aldehydes that we are aware of are those of Landais: Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 23, 4037-4053. Landais, Y.; Zekri, E. Tetrahedron Lett. 2001, 42, 6547-6551.
21. Landais, Y. In Organometallics; Compounds of Group 15 (As, Sb, Bi) and Silicon Compounds; Fleming, I., Ed.; Georg Thieme Verlag: New York, 2000; Vol. 4, pp 757-771.
22. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444-4448. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251-6253. Sato, T.; Matsumoto, K.; Abe, T. ; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167-2170. Review: Larson, G. L. Adv. Silicon Chem. 1996, 3, 105-271.
23. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444-4448. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251-6253. Sato, T.; Matsumoto, K.; Abe, T. ; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167-2170. Review: Larson, G. L. Adv. Silicon Chem. 1996, 3, 105-271.
24. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444-4448. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251-6253. Sato, T.; Matsumoto, K.; Abe, T. ; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167-2170. Review: Larson, G. L. Adv. Silicon Chem. 1996, 3, 105-271.
25. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444-4448. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251-6253. Sato, T.; Matsumoto, K.; Abe, T. ; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167-2170. Review: Larson, G. L. Adv. Silicon Chem. 1996, 3, 105-271.
26. Use of this methodology with analogues of 15 in which the tert-butyldimethylsilyl group has been replaced with trimethylsilyl, dimethylphenylsilyl, or methyldiphenylsilyl has not resulted in acceptable yields of the corresponding amino acids. Efforts to optimize this chemistry for other substrates is continuing.