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Volumn 3, Issue 9, 1997, Pages 1432-1441

A contribution to the asymmetric synthesis of 3-amine β-lactams: The diastereoselective [2+2] cycloaddition reaction of chiral aminoketene equivalents with enolizable aldehyde-derived/mines

Author keywords

Asymmetric synthesis; Cycloadditions; Imines; Lactams; Silicon

Indexed keywords


EID: 0030870477     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030909     Document Type: Article
Times cited : (54)

References (79)
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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
    • 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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    • 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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    • 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.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9027
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    • note
    • 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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