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C,C-bis(trimethylsilyl)methylamine can be prepared in gram quantities from commercially available N,N-dimethylcyanamide or cyanotrimethylsilane: a) J. P. Picard, S. Grelier, T. Constantieux, J. Dunoguès, J. M. Aizpurua, C. Palomo, M. Petraud, B. Barbe, L. Lunnazi, J. M. Leger, Organometallics, 1993, 12, 1378; b) S. Grelier, T. Constantieux, D. Deffieux, M. Bordeau, J. Dunoguès, J. P. Picard, C. Palomo, J. M. Aizpurua, Organometallics 1994, 13, 3711, and also from bis(trimethyl silyl)chloromethane, see: C. Palomo, J. M. Aizpurua, J. M. Garcia, M. Legido, J. Chem. Soc. Chem. Commun. 1991, 524.
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C,C-bis(trimethylsilyl)methylamine can be prepared in gram quantities from commercially available N,N-dimethylcyanamide or cyanotrimethylsilane: a) J. P. Picard, S. Grelier, T. Constantieux, J. Dunoguès, J. M. Aizpurua, C. Palomo, M. Petraud, B. Barbe, L. Lunnazi, J. M. Leger, Organometallics, 1993, 12, 1378; b) S. Grelier, T. Constantieux, D. Deffieux, M. Bordeau, J. Dunoguès, J. P. Picard, C. Palomo, J. M. Aizpurua, Organometallics 1994, 13, 3711, and also from bis(trimethyl silyl)chloromethane, see: C. Palomo, J. M. Aizpurua, J. M. Garcia, M. Legido, J. Chem. Soc. Chem. Commun. 1991, 524.
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C,C-bis(trimethylsilyl)methylamine can be prepared in gram quantities from commercially available N,N-dimethylcyanamide or cyanotrimethylsilane: a) J. P. Picard, S. Grelier, T. Constantieux, J. Dunoguès, J. M. Aizpurua, C. Palomo, M. Petraud, B. Barbe, L. Lunnazi, J. M. Leger, Organometallics, 1993, 12, 1378; b) S. Grelier, T. Constantieux, D. Deffieux, M. Bordeau, J. Dunoguès, J. P. Picard, C. Palomo, J. M. Aizpurua, Organometallics 1994, 13, 3711, and also from bis(trimethyl silyl)chloromethane, see: C. Palomo, J. M. Aizpurua, J. M. Garcia, M. Legido, J. Chem. Soc. Chem. Commun. 1991, 524.
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note
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The same trend was observed in the reaction of 14 with N-p-methoxyphenyl and N-benzyl glyoxylate imines, thus indicating that this anomalous behaviour of Evans-Sjögren ketenes is inherent in these kind of imines. No reason for this has been found yet.
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63
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For an ester enolate-imine approach to carumonam using glycoaldehyde imines, see: L. E. Overman, T. Osawa, J. Am. Chem. Soc. 1985, 107, 1698.
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Overman, L.E.1
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64
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For another paper documenting this aspect, see: D. Dugat, G. Just, S. Sahoo, Can. J. Chem. 1987, 65, 88.
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0342951793
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ref. [3]
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4 side chain for further ring closure. For detailed information on this subject, see: R. D. G. Cooper in ref. [3], p. 272.
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Cooper, R.D.G.1
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66
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J. Lasarte, C. Palomo, J. P. Picard, J. Dunoguès, J. M. Aizpurua, J. Chem. Soc. Chem. Commun. 1989, 72.
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L. S. Hegedus, J. Montgomery, Y. Narukawa, D. C. Snustad, J. Am. Chem. Soc. 1991, 113, 5784.
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The mixture of 30/31 was not separated. The cis/trans ratio was determined on the basis of coupling constants and epimerization at the C 3 position was assigned on the basis of previous observations made on related compounds; see: C. Palomo, J. M. Aizpurua, C. Cuevas, A. Mielgo, R. Galarza, Tetrahedron Lett. 1995, 36, 9027.
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0343387211
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note
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3) and the ketene derived from 14 gave no trace of the expected N-trimethylsilylmethyl-β-lactam, showing that the presence of two α-silyl groups was necessary to promote the azetidin-2-one formation. Instead, the enamide 38 was the only isolable pure compound of such a reaction in 28% yield. (Equation Presented)
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75
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