Formate ester synthesis via reaction of 2-bromoethylamines with dimethylformamide

Tetrahedron Letters

Volumn 49, Issue 10, 2008, Pages 1648-1651

  Dakanali, Marianna ^a   Tsikalas, George K ^a   Krautscheid, Harald ^b   Katerinopoulos, Haralambos E ^a  

^a UNIVERSITY OF CRETE   (Greece)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

2 Bromoethylamines; Aziridinium ion; Formate esters; Vilsmeier intermediate

Indexed keywords

2 BROMOETHYLAMINE DERIVATIVE; AZIRIDINE DERIVATIVE; BETA AMINO ACID; FORMIC ACID DERIVATIVE; N,N DIMETHYLFORMAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; STEREOCHEMISTRY;

EID: 38949166702     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.002     Document Type: Article

References (19)

1. Dakanali M., Roussakis E., Kay A.R., and Katerinopoulos H.E. Tetrahedron Lett. 46 (2005) 4193
2. De Luca L., Giacomelli G., and Porcheddu A. J. Org. Chem. 67 (2002) 5152
3. Koeller S., and Lellouche J.-P. Tetrahedron Lett. 40 (1999) 7043
4. Hedvati L., Nudelman A., Falb E., Kraiz B., Zhuk R., and Sprecher M. Eur. J. Med. Chem. 37 (2002) 607
5. Shi M., and Shen Y.-M. Molecules 7 (2002) 386
6. Chang R.K., and Kim K. Tetrahedron Lett. 41 (2000) 8499
7. Dangeli F., Cavicchioni G., Catelani G., Marchetti P., and Maran F. Gazz. Chim. Ital. 119 (1989) 471
8. Nagle A.S., Salvatore R.N., Chong B.-D., and Jung K.W. Tetrahedron Lett. 41 (2000) 3011
9. Hwang C.K., Li W.S., and Nicolaou K.C. Tetrahedron Lett. 25 (1984) 2295
10. 3. Programs for structure solution and refinement: shelxs-97 (Sheldrick, 1990) and shelxl-97 (Sheldrick, 1997); Graphical presentation: Diamond2 (Brandenburg, 1999).
11. For a related mechanism, see:. Metro T.-X., Appenzeller J., Pardo D.G., and Cossy J. Org. Lett. 8 (2006) 3509 and references cited therein
12. Couturier C., Blanchet J., Schlama T., and Zhu J. Org. Lett. 8 (2006) 2183 In this case, the diprotected 2-aminoalcohols, with the amino group at a secondary center, lead to the exclusive formation of the corresponding rearranged β-amino esters with complete stereochemical inversion at the secondary centers
13. 13C NMR, IR and MS) data. Crystallographic data (excluding structure factors) for (R)-14 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication Number CCDC 661281. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
14. Shaw G. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 7 (1996), Pergamon, New York 397
15. Bergmeier S.C. Tetrahedron 56 (2000) 2561
16. Muñiz K. Chem. Soc. Rev. 33 (2004) 166
17. Bodkin J.A., and McLeod M.D. J. Chem. Soc., Perkin Trans. 1 (2002) 2733
18. Li G., Chang H.-T., and Sharpless K.B. Angew. Chem., Int. Ed. Engl. 35 (1996) 451
19. Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., and Olah G.A. Org. Lett. 2 (2000) 3173