-
3
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-
33750699374
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-
For recent examples of the use of the Bruylants reaction and its variations in synthesis, see:
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4
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22144437423
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11
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12
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Tagat J.R., Steensma R.W., McCombie S.W., Nazareno D.V., Lin S.-I., Neustadt B.R., Cox K., Xu S., Wojcik L., Murray M.G., Vantuno N., Baroudy B.M., and Striski J.M. J. Med. Chem. 44 (2001) 3343-3346
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29
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33750688916
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note
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This is in marked contrast with the vast number of examples of non-racemic aminonitriles which contain two or more stereogenic centres. For some illustrations, see Ref. 3.
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31
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33750720706
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Hylton, T. A.; Shenton, F. L. U.S. Patent 4,072,698, 1978;
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33750724193
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Matthews, G. French Patent 2141354, 1973;
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Sonke T., Kaptein B., Wagner A.F.V., Quaedflieg P.J.L.M., Schultz S., Ernste S., Schepers A., Mommers J.H.M., and Broxterman Q.B. J. Mol. Catal. B: Enzym 29 (2004) 265-277
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Sonke, T.1
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Schultz, S.5
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Schepers, A.7
Mommers, J.H.M.8
Broxterman, Q.B.9
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38
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33750714136
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For reviews, see:
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40
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0041378065
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Gröger H. Chem. Rev. 103 (2003) 2795-2827
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Gröger, H.1
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41
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33750691730
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Schmalz H.-G., and Wirth T. (Eds), Wiley-VCH, Weinheim
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Yet L. In: Schmalz H.-G., and Wirth T. (Eds). Organic Synthesis Highlights V (2003), Wiley-VCH, Weinheim 187-193
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Organic Synthesis Highlights V
, pp. 187-193
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Yet, L.1
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43
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0034624418
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An example of a one-pot three-component enantioselective Strecker reaction has been described, but the amine involved is an aniline, which therefore gives an N-monosubstituted aminonitrile, see:
-
An example of a one-pot three-component enantioselective Strecker reaction has been described, but the amine involved is an aniline, which therefore gives an N-monosubstituted aminonitrile, see:. Ishitani H., Komiyama S., Hasegawa Y., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 762-766
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Ishitani, H.1
Komiyama, S.2
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Kobayashi, S.4
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61
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33750719703
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3 or TFAA, apparently with total diastereoisomeric control, see:
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64
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33750733349
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-
Compounds 2 are available commercially, although they can be expensive. As an alternative they can be prepared from the corresponding aminoacids using standard operations, see:
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65
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37049077093
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Lagriffoul P.-H., Tadros Z., Taillades J., and Commeyras A. J. Chem. Soc., Perkin Trans. 2 (1992) 1279-1285
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71
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33750689932
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note
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Occasionally, the crude isolate had a small but non-zero optical rotation. This is explained by the presence of traces of the chiral carboxamide 3, carried through with the aminonitrile 1; the carboxamides are apparently not transformed in the Bruylants conditions. In such cases, the presence of the carboxamide was confirmed by GLC analysis of the crude Bruylants reaction product mixture.
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72
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Benson S.C., Cai P., Colon M., Haiza M.A., Tokles M., and Snyder J.K. J. Org. Chem. 53 (1988) 5335-5341
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Snyder, J.K.6
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73
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84989478191
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We are aware of only one description of a series of Bruylants reactions which appear to have been carried out using 1.1 equiv of Grignard reagents. The substrates were α-secondary allylic α-aminonitriles and reported yields of amines averaged around 60%, see:
-
We are aware of only one description of a series of Bruylants reactions which appear to have been carried out using 1.1 equiv of Grignard reagents. The substrates were α-secondary allylic α-aminonitriles and reported yields of amines averaged around 60%, see:. Ahlbrecht H., and Dollinger H. Synthesis (1985) 743-748
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Synthesis
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Dollinger, H.2
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Lindsell W.E. In: Wilkinson G., Stone F.G.A., and Abel E.W. (Eds). Comprehensive Organometallic Chemistry II Vol. 1 (1995), Pergamon, Oxford 57-127
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Lindsell, W.E.1
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