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Merchan, F.L.4
Tejero, T.5
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70
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and references therein
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For reviews on the 1,3-addition of organometallic reagents to nitrones, see: (c) Lombardo, M.; Trombini, C. Curr. Org. Chem. 2002, 6, 695-713 and references therein.
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Jackman, L. M., Sternhell, S., Eds.; Pergamon: Elmsford, NY
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13C NMR spectra of compounds 5a,b and 6a,b, in which a N-Cbz group is present, showed doubling of signals. This was due to isomerization by restricted rotation around C=N, see: Applications of NMR spectroscopy in organic chemistry; Jackman, L. M., Sternhell, S., Eds.; Pergamon: Elmsford, NY, 1978; p 361.
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Applications of NMR Spectroscopy in Organic Chemistry
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72
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2 in acetonitrile-water is known to give D-glucose-substituted N-benzyl-protected α-amino aldehydes; see: (a) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem.-Eur. J. 1995, 1, 505-520.
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Tejero, T.6
Bertolasi, V.7
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(b) Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496.
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Scherrmann, M.-C.5
Tejero, T.6
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0344447095
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Our results were found to be identical with that reported by J. Jurczak and co-workers in which the addition of vinylmagnesium bromide to -N(Bn)Cbz diprotected L-alaninal afforded syn/anti products in the ratio 23:77; see: (a) Gryko, D.; Urbanczyk-Lipkowska, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 4059-4067.
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Gryko, D.1
Urbanczyk-Lipkowska, Z.2
Jurczak, J.3
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76
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33744920405
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-
note
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2O at -50 °C afforded a 1:1 mixture of the anti/syn products in low yield. Performing the reaction at 0 °C also led to the same ratio, with a low combined yield (55%).
-
-
-
-
77
-
-
33744937164
-
-
note
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The reaction at 0 °C also afforded a single diastereomer.
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-
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78
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0023043811
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Houck, K. N.; Paddon-Row, N. M.; Rondon, N. G.; Wu, Y. D.; Brown, F. K.; Spellmeyer, C. D.; Metz, J. T.; Li, Y. L.; Loncharich, R. J. Science 1986, 231, 1108-1117.
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Houck, K.N.1
Paddon-Row, N.M.2
Rondon, N.G.3
Wu, Y.D.4
Brown, F.K.5
Spellmeyer, C.D.6
Metz, J.T.7
Li, Y.L.8
Loncharich, R.J.9
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