Subscribe to RSS
DOI: 10.1055/s-0029-1216959
Synthesis of β-Oxabutyrolactams Starting from 2,5-Dihydrooxazoles
Publication History
Publication Date:
21 August 2009 (online)
Abstract
A new synthetic pathway to generate β-oxabutyrolactams starting from 2,5-dihydrooxazoles is described. This procedure is based on the addition of acid chlorides to heterocyclic imines followed by oxidation in the presence of pyridinium chlorochromate.
Key words
heterocycles - imines - β-oxabutyrolactams - oxidation - N-acyliminium ion
- 1
Karrer F. inventors; Eur. Pat. Appl. EP 79850. ; Chem. Abstr. 1983, 99, 123617 - 2
Middleton WJ. inventors; US 3690862. ; Chem. Abstr. 1972, 78, 12689 - 3
Saito T,Murayama T,Matsumoto T, andMiura T. inventors; Eur. Pat. Appl. EP 974582. ; Chem. Abstr. 2000, 132, 107824 -
4a
Eichenberger K.Ganz E.Druey J. Helv. Chim. Acta 1955, 38: 284 -
4b
Hiskey RG.Jung JM. J. Am. Chem. Soc. 1963, 85: 578 -
4c
Roush WR.Essenfeld AP.Warmus JS.Brown BB. Tetrahedron Lett. 1989, 30: 7305 -
4d
Thompson AM.Blunt JW.Munro MHG.Clark BM. J. Chem. Soc., Perkin Trans. 1 1994, 1025 -
5a
Holzgrabe U. Pharm. Unserer Zeit 2006, 35: 410 -
5b
Elander RP. Appl. Microbiol. Biotech. 2003, 61: 385 - 6
Weber M.Jakob J.Martens J. Liebigs Ann. Chem. 1992, 1 - 7
Harada K. Additions to the azomethine group, In The chemistry of the carbon-nitrogen double bondPatai S. John Wiley & Sons; London: 1970. p.255 - 8
Yazici A.Pyne SG. Synthesis 2009, 339 - 9
Speckamp WN.Hiemstra H. Tetrahedron 1985, 41: 4367 - 10
James TC.Judd CW. J. Chem. Soc., Trans. 1914, 105: 1427 - 11
Leuchs H.Wulkow G.Gerland H. Chem. Ber. 1932, 62: 1586 - 12
Maryanoff BE.Zhang H.-C.Cohen JH.Turchi IJ.Maryanoff CA. Chem. Rev. 2004, 104: 1431 - 13
Bose AK.Spiegelman G.Manhas MS. Tetrahedron Lett. 1971, 34: 3167 - 16
Belyaev A.Borloo M.Augustyns K.Lambeir A.-M.De Meester I.Scharpé S.Blaton N.Peeters OM.De Ranter C.Haermers A. Tetrahedron Lett. 1995, 36: 3755 - 17
Hatam M.Tehranfar D.Martens J. Synthesis 1994, 619
References
In the major diastereomers, saturation of the protons of the methyl moiety at C5 generates a very small NOE for the proton at C4, indicating trans-configuration. Compared to the ROE experiments of the minor diastereomers, the saturation of the protons of the methyl moiety at C5 led to a strong NOE for the proton at C4, consequently indicating cis-configuration.
15Saturation of the protons of the methyl group at C5 (˜1 ppm) gave a strong NOE for the proton at C4 and a moderate NOE for the proton at C2, indicating cis-configuration for the protons at C2 and C4.