Characterization of β-Amino Ester Enolates as Hexamers via 6Li NMR Spectroscopy

Journal of the American Chemical Society

Volumn 126, Issue 19, 2004, Pages 5938-5939

  McNeil, Anne J ^a   Toombes, Gilman E S ^b   Chandramouli, Sithamalli V ^c   Vanasse, Benoit J ^c   Ayers, Timothy A ^c   O'Brien, Michael K ^c   Lobkovsky, Emil ^a   Gruner, Sol M ^b   Marohn, John A ^a   Collum, David B ^a  

^a Department of Obstetrics Gynecology   (United States)

^b Cornell University   (United States)

^c SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BETA AMINO ESTER ENOLATE; ESTER DERIVATIVE; HEXAMER; LITHIUM; POLYMER; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAMETER;

ALKYLATION; AMINO ALCOHOLS; INDICATORS AND REAGENTS; ISOTOPES; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; TEMPERATURE;

EID: 2442609869     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049245s     Document Type: Article

References (26)

1. Enolization was effected without N-lithiation using LiHMDS. Chandramouli, S. V.; O'Brien, M. K.; Powner, T. H. WO Patent 0040547, 2000. See also: Czekaj, M.; Klein, S. I.; Guertin, K. R.; Gardner, C. J.; Zulli, A. L.; Pauls, H. W.; Spada, A. P.; Cheney, D. L.; Brown, K. D.; Colussi, D. J.; Chu, V.; Leadley, R. J.; Dunwiddie, C. T. Bioorg. Med. Chem. Lett. 2002, 12, 1667-1670. Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527-3529. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am Chem. Soc. 1995, 117, 8488-8489.
2. Enolization was effected without N-lithiation using LiHMDS. Chandramouli, S. V.; O'Brien, M. K.; Powner, T. H. WO Patent 0040547, 2000. See also: Czekaj, M.; Klein, S. I.; Guertin, K. R.; Gardner, C. J.; Zulli, A. L.; Pauls, H. W.; Spada, A. P.; Cheney, D. L.; Brown, K. D.; Colussi, D. J.; Chu, V.; Leadley, R. J.; Dunwiddie, C. T. Bioorg. Med. Chem. Lett. 2002, 12, 1667-1670. Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527-3529. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am Chem. Soc. 1995, 117, 8488-8489.
3. Enolization was effected without N-lithiation using LiHMDS. Chandramouli, S. V.; O'Brien, M. K.; Powner, T. H. WO Patent 0040547, 2000. See also: Czekaj, M.; Klein, S. I.; Guertin, K. R.; Gardner, C. J.; Zulli, A. L.; Pauls, H. W.; Spada, A. P.; Cheney, D. L.; Brown, K. D.; Colussi, D. J.; Chu, V.; Leadley, R. J.; Dunwiddie, C. T. Bioorg. Med. Chem. Lett. 2002, 12, 1667-1670. Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527-3529. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am Chem. Soc. 1995, 117, 8488-8489.
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23. For more examples of ester enolate crystal structures, see: Williard, P. G. Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1, pp 1-47. Seebach, D. Angew Chem., Int. Ed. Engl. 1988, 27, 1624-1654. Boche, G.; Langlotz, I.; Marsch, M.; Harms, K. Chem. Ber. 1994, 127, 2059-2064. Jastrzebski, J. T. B. H.; van Koten, G.; van de Mieroop, W. F. Inorg. Chim. Acta 1988, 142, 169-171.
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