A new simple route for the synthesis of (±)-2-azetidinones starting from β-enaminoketoesters

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 6995-6998

  De Risi, Carmela ^a   Pollini, Gian P ^a   Veronese, Augusto C ^a   Bertolasi, Valerio ^b  

^a Dipto di Scienze Farmaceutiche   (Italy)

^b Dipartimento Chimico   (Italy)

Author keywords

Enaminoketoesters; 2 Azetidinones

Indexed keywords

2 AZETIDINONE DERIVATIVE; ACETOACETIC ACID DERIVATIVE; ALKYL GROUP; ASPARTIC ACID DERIVATIVE; BETA LACTAM DERIVATIVE; ESTER DERIVATIVE; FORMIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033578837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01421-5     Document Type: Article

References (7)

1. The Organic Chemistry of β-Lactams, Georg, G. I. Ed.; VCH, New York, 1993.
2. Kidwai, M.; Sapra, P.; Bhushan, K. R., Curr. Med. Chem., 1999, 6, 195.
3. Corain B.; Basato M.; Veronese A.C. J. Mol. Catalysis, 1993, 81, 133.
4. Veronese A.C.; Gandolfi V.; Longato B.; Corain B.; Basato M. J. Mol. Catalysis, 1989, 54, 73.
5. Veronese A.C.; Callegari R., Morelli C.F., Vicentini C.B. Tetrahedron, 1997, 53, 14497.
6. 3) δ: -4.08 (q, J=118 Hz), -4.28 (q, J=118 Hz), 14.10 (q, J=126 Hz), 17.95 (s), 20.62 (q, J=126 Hz), 25.67 (q, J=124 Hz), 50.03 (d, J=154 Hz), 61.52 (t, J=147 Hz), 63.85 (d, J=139 Hz), 64.93 (d, J=141 Hz), 167.46 (s, COO), 171.53 (s, COO).
7. -3. Intensity data collected with θ ≤ 27 ° using Mo Kα radiation (0.71073 Å) on an Enraf-Nonius CAD4 diffractometer; T = 295 K, 3310 independent reflections measured; 1426 reflections observed [I ≥ 3σ(I)]; solution by direct methods; full matrix least-squares refinement using SHELXL-97 (Sheldrick, G. M. SHELX1-97. Program for the Refinement for Crystal Structures. University of Göttingen, Germany, 1997); non-hydrogens anisotropic, methyl hydrogens atoms included at calculated positions and the remaining hydrogens refined isotropically. An ORTEP view of the molecule (Johnson, C. K., ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976) is shown in Figure. The molecules in the crystal are connected by two hydrogen bonds: O2-H20 - O1 [O2-H20 = 0.95(7), O2 - O1(3/2-x, y-1/2, 1-z) = 2.693(7) Å, O2-H20 - O1 = 175(6)°] and N1-H1 - O2 [N1-H1 = 0.88(5), N1 - O2 (2-x, -y, 1-z) = 2.844(7) Å, N1-H1 - O2 = 156(5)°]. Atomic coordinates, thermal parameters, bond lengths and angles are available from the Cambridge Crystallographic Data Centre.