Reaction of α-amidoalkylphenyl sulfones with Reformatsky reagents. A new entry to β-amino esters

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2709-2712

  Mecozzi, Tiziana ^a   Petrini, Marino ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Amino acids and derivatives; N imides; Reformatsky reagents; Sulfones

Indexed keywords

AMINO ACID DERIVATIVE; ESTER DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; ITALY; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034620956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00245-8     Document Type: Article

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29. Stereochemical assignments for some compounds 3 have been done by comparison with literature data: Seebach, D.; Abele, S.; Gademann, K.; Guichard, G.; Hintermann, T.; Jaun, B.; Mattews, J. L.; Schreiber, J. V. Helv. Chim. Acta 1998, 81, 932-982. The chemical shift of the N-H proton for the syn isomer is usually around 5.4 ppm while that for the anti isomer is around 4.9 ppm.
30. 1H NMR δ: 0.89 (t, 3H, J=7.3 Hz), 1.24 (t, 3H, J=7.1 Hz), 1.46 (s, 9H), 1.60-1.90 (m, 4H), 2.45-2.50 (m, 1H), 2.60-2.80 (m, 2H), 3.75-3.90 (m, 1H), 4.13 (q, 2H, J=7.1 Hz), 4.64 (d, 1H, J=9.9 Hz), 7.15-7.35 (m, 5H).