Nucleophilic alkynylation of N-bis(trimethylsilyl)methyl aldimines

Tetrahedron Letters

Volumn 48, Issue 23, 2007, Pages 4135-4138

  Wee, Andrew G H ^a   Zhang, Bao ^a  

^a UNIVERSITY OF REGINA   (Canada)

Author keywords

Alkynylation; N Bis(trimethylsilyl)methyl aldimine; N BTMSM

Indexed keywords

ALKYNE DERIVATIVE; AMINE; IMINE; LITHIUM ALKYNIDE DERIVATIVE; N BIS(TRIMETHYLSILYL)METHYL ALDIMINE DERIVATIVE; N BIS(TRIMETHYLSILYL)METHYL PROPARGYL AMINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYNYLATION; ARTICLE; CHEMICAL STRUCTURE;

EID: 34247867852     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.171     Document Type: Article

References (41)

1. Maier M.E., Boße F., and Neistroj A.J. Eur. J. Org. Chem. (1999) 1
2. Konishi M., Ohkuma H., Tsuno T., Oki T., VanDuyne G.D., and Clardy J. J. Am. Chem. Soc. 112 (1990) 3715
3. Hutchinson J.H., Cook J.J., Brashear K.M., Breslin M.J., Glass J.D., Gould R.J., Halczenko W., Holahan M.A., Lynch R.J., Sitko G.R., Stranieri M.T., and Hartman G.D. J. Med. Chem. 39 (1996) 4583
4. Hoekstra W.J., Maryanoff B.E., Damiano B.P., Andrade-Gordon P., Cohen J.H., Costanzo M.J., Haertlein B.J., Hecker L.R., Hulshizer B.L., Kauffman J.A., Keane P., McComsey D.F., Mitchell J.A., Scott L., Shah R.D., and Yabut S.C. J. Med. Chem. 42 (1999) 5254
5. Kauffamn G.S., Harris G.D., Dorow R.L., Stone B.R.P., Parsons Jr. R.L., Pesti J.A., Magnus N.A., Fortunak J.M., Confalone P.N., and Nugent W.A. Org. Lett. 2 (2000) 3119
6. Reginato G., Mordini A., and Caracciolo M. J. Org. Chem. 62 (1997) 6187
7. Poerwono H., Higashiyama K., and Takahashi H. J. Org. Chem. 63 (1998) 2711
8. Comins D.L., Stolze D.A., Thakkar P., and McArdle C.L. Tetrahedron Lett. 39 (1998) 5693
9. Koradin C., and Knochel P. Chem. Eur. J. 9 (2003) 2797
10. Olivi N., Spruyt P., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 45 (2004) 2607
11. Bloch R. Chem. Rev. 98 (1998) 1407
12. Dodda R., and Zhao C.-G. Org. Lett. 9 (2007) 165
13. Lee Y.K., Lee C.G., Na J.E., and Kim J.N. Tetrahedron Lett. 46 (2005) 69
14. Fischer C., and Carreira E.M. Org. Lett. 3 (2001) 4319
15. Jiang B., and Si Y.-G. Tetrahedron Lett. 44 (2003) 6767
16. For asymmetric approaches:. Iguchi M., Yamada K.-I., and Tomioka K. Top. Organomet. Chem. 5 (2003) 37
17. Blanchet J., Bonin M., and Micouin L. Org. Prep. Proceed. Int. 34 (2002) 467
18. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069
19. Bisai A., and Singh V.K. Org. Lett. 8 (2006) 2405
20. Wei C., Mague J.T., and Li C.J. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5744
21. Boezio A.A., Solberghe G., Lauzon C., and Charette A.B. J. Org. Chem. 68 (2003) 3241 and references cited therein
22. Traverse J.F., Hoveyda A.H., and Snapper M.L. Org. Lett. 5 (2003) 3273
23. Shimizu M., Kawamoto M., and Niwa Y. Chem. Commun. (1999) 1151
24. Picard J.-P. Can. J. Chem. 78 (2000) 1363
25. Palomo C., Aizpurua J.M., Legido M., Galarza R., Deya P.M., Dunogues J., Picard J.-P., Ricci A., and Seconi G. Angew. Chem., Int. Ed. 35 (1996) 1239
26. Palomo C., Aizpurua J., Ganboa I., Benito A., Cuerdo L., Fratila R.M., Jimenez A., Loinaz I., Miranda J.I., Pytlewska K.R., Micle A., and Linden A. Org. Lett. 6 (2004) 4443
27. Ricci A., Guerrini A., Seconi G., Mordini A., Constantieux T., Picard J.-P., Aizpurua J.M., and Palomo C. Synlett (1994) 955
28. Bonini B.F., Fochi M., Franchini M.C., Mazzanti G., Ricci A., Picard J.-P., Dunogues J., Aizpurua J.M., and Palomo C. Synlett (1997) 1321
29. Wee A.G.H., Duncan S.C., and Fan G.-J. Tetrahedron: Asymmetry 17 (2006) 297
30. Wee A.G.H., and Duncan S.C. J. Org. Chem. 70 (2005) 8372
31. Doyle M.P., Hu W., Wee A.G.H., Wang Z., and Duncan S.C. Org. Lett. 5 (2003) 407
32. The N-BTMSM imines are chromatographically stable compounds with the exception of 1b wherein isomerization to the enamine was observed during chromatography. Aldehyde 1e was prepared via ozonolysis of bis(MOM) ether of cis-2-butene-1,4-diol:. Christine S., Anna-Maria L., Dominique P., Gerard A., Daniel A., Dieter W., and Guenter H. Bull. Soc. Chim. Fr. 131 (1994) 831
33. Yamaguchi M., and Hirao I. Tetrahedron Lett. 24 (1983) 1719
34. Wada M., Sakurai Y., and Akiba K. Tetrahedron Lett. 25 (1984) 1083
35. Aubrecht K.B., Winemiller M.D., and Collum D.B. J. Am. Chem. Soc. 122 (2000) 11084
36. 4. After filtration, the solvent was evaporated in vacuo and the residue was purified by flash column chromatography.
37. 3, 75 MHz): δ -0.1, 0.1, 36.8, 40.3, 55.4, 58.0, 70.2, 96.5, 111.0, 114.8, 121.0, 124.0, 124.3, 129.9, 137.5, 143.8.
38. 3 in the present study.
39. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045
40. Kirsch G., Hesse S., and Comel A. Curr. Org. Syn. 1 (2004) 47
41. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873