Selectivity aspects of the ring opening reaction of 2-alkenyl aziridines by carbon nucleophiles

Tetrahedron Letters

Volumn 46, Issue 15, 2005, Pages 2539-2542

  Cunha, Rodrigo L O R ^a   Diego, Dennis G ^b   Simonelli, Fábio ^b   Comasseto, João V ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

Author keywords

2 Alkenyl aziridines; Organometallics; Ring opening

Indexed keywords

ALKENYL GROUP; AZIRIDINE DERIVATIVE; CARBON; ORGANOMETALLIC COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; MASS SPECTROMETRY; METALLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 15244353940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.089     Document Type: Article

References (31)

1. D. Tanner Angew. Chem., Int. Ed. Engl. 33 1994 599
2. W. McCoull, and F.A. Davis Synthesis 2000 1347
3. V.H. Dahanukar, and I.A. Zavialov Curr. Opin. Drug Discovery Dev. 5 2002 918
4. X.E. Hu Tetrahedron 60 2004 2701
5. C.S. Penkett, and I.D. Simpson Tetrahedron Lett. 42 2001 1179
6. N. Fujii, K. Nakai, H. Tamamura, A. Otaka, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto, and T. Ibuka J. Chem. Soc., Pekin Trans. 1 1995 1359
7. T. Hudlicky, X.R. Tian, K. Konisberger, R. Maurya, J. Rouden, and B. Fan J. Am. Chem. Soc. 118 1996 10752
8. F. Gini, F. Del Moro, F. Macchia, and M. Pineschi Tetrahedron Lett. 44 2003 8559
9. M.B. Smith Organic Synthesis 2nd ed. 2002 McGraw-Hill Boston
10. M. Schlosser Organometallics in synthesis-a manual 1st ed. 1996 John Wiley & Sons New York
11. E. Baron, P. O'Brien, and T.D. Towers Tetrahedron Lett. 43 2002 723
12. Original procedure: J.K. Knight, and M.P. Muldowney Synlett 1995 949
13. -1) 2940, 2845, 2590, 2464, 1595, 1492, 1319, 1292, 1158, 1091, 1027, 950, 865, 821, 810, 771, 705, 672, 598, 557, 534
14. -1) 3282, 2926, 2857, 1599, 1428, 1327, 1161, 1095, 1046, 972, 815, 665, 552
15. C.M. Williams, and L.N. Mander Tetrahedron 57 2001 425
16. The differences between the results obtained for the BuLi/CuCN (20 mol %) system (entry 4) and for the Lipshutz cuprate (entry 11) is probably due to the nature of the organometallic species present in each system. Albeit the reagents, a priori, could be considered as the same in both systems, excess of BuLi in combination with CuCN can generate organocuprates with several stoichiometries in solution, different from those present in the reaction media of the pre-formed Lipshutz cuprate. For a more detailed discussion, see: E. Nakamura, and N. Yoshikai Bull. Chem. Soc. Jpn. 77 2004 1 and references cited therein
17. B.H. Lipshutz, K. Woo, T. Gross, D.J. Buzard, and R. Tirado Synlett 1997 477
18. T. Harada, and A. Oku Preparation and Reaction of Triorganozincates P. Knochel P. Jones Organozinc Chemistry-a Practical Approach Practical Approach in Chemistry Series 1999 Oxford New York 101 116
19. Procedure adapted from: J.A. Marshal, and P. Eidam Org. Lett. 6 2004 445 In this work the authors used an alkenyl iodide as vinylic moiety source of vinyllithium, we used instead a vinylic telluride as a vinyl moiety source
20. P. Knochel, and B. Betzemeier Transmetallation reactions producing organocopper reagents N. Krause Modern Organocopper Chemistry 2002 Wiley-VCH Weinheim 45 78
21. T.-L. Ho Tetrahedron 41 1985 1
22. 4, filtered and concentrated to afford a colourless oil
23. 3, δ in ppm) δ 143.2, 138.2, 134.5, 129.6, 126.9, 126.3, 47.3, 45.6, 32.5, 29.2, 28.4, 27.8, 27.2, 21.5, 18.6
24. F.C. Tucci, A. Chieffi, J.V. Comasseto, and J.P. Marino J. Org. Chem. 61 1996 4975
25. J.A. Marshall Chem. Rev. 89 1989 1503
26. T.L. Underiner, and H.L. Goering J. Org. Chem. 54 1989 3239
27. C. Gallina Tetrahedron Lett. 23 1982 3093
28. B. Breit, and P. Demel Adv. Synth. Catal. 343 2001 429
29. M. Pineschi New J. Chem. 28 2004 657
30. H. Booth, J.R. Everett, and R.A. Fleming Org. Magn. Res. 12 1979 63
31. 3, δ in ppm) δ 143.1, 137.7, 131.0, 129.4, 126.9, 124.3, 77.1, 55.6, 51.6, 25.1, 22.6, 21.4