Readily available unprotected amino aldehydes

Journal of the American Chemical Society

Volumn 128, Issue 46, 2006, Pages 14772-14773

  Hili, Ryan ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; FUNCTIONAL GROUP;

AMINATION; ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; DIASTEREOISOMER; REDUCTION; RING OPENING; SYNTHESIS; THERMODYNAMICS;

EID: 33845230631     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065898s     Document Type: Article

References (17)

1. Rappoport, Z., Ed. The Chemistry of Enamines; John Wiley & Sons: New York, 1994.
2. For reviews on N-protected amino aldehydes see (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
3. (b) Reetz, M. T. Angew. Chem., Int Ed. 1991, 30, 1531.
4. (c) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 1825.
5. (a) D-Glucosamine, a naturally occurring amino aldehyde, is stable as a cyclic aminal salt: Fischer, E.; Leuchs, H. Ber. Dtsch. Chem. Ges. 1902, 36, 24.
6. (b) Glycinal was characterized through degradation studies: Fischer, E. Ber. 1908, 41, 956.
7. Fischer, E. Ber. 1908, 41, 1019.
8. (c) For a preparation of histidinal dihydrochloride, see Adams, E. J. Biol. Chem. 1955, 217, 317.
9. Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3236.
10. Ooi, T.; Saito, A.; Maruoka, J. J. Am. Chem. Soc. 2003, 125, 3220.
11. Strained iminium ions derived from aziridines can be formed under forcing conditions. See Daly, J. J. Org. Chem. 1970, 35, 1861.
12. See Davis, F. A. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; John Wiley & Sons: New York, 2006.
13. (a) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881.
14. (b) Serafin, S. V.; Zhang, K.; Aurelio, L.; Hughes, A. B.; Morton, T. H. Org. Lett. 2004, 6, 1561.
15. Hesse, M. Alkaloids: Nature's Curse or Blessing?; John Wiley & Sons: New York, 2002.
16. For application of tryptamine derivatives in the Pictet-Spengler reaction, see Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
17. We have observed no evidence for epimerization of the amino aldehyde α-stereocenter under basic or acidic conditions.