Synthesis 2013; 45(6): 773-776
DOI: 10.1055/s-0032-1316860
paper
© Georg Thieme Verlag Stuttgart · New York

α-Carboxy-β-Lactones from Photoinduced Ring Contraction of 3-Diazodihydrofuran-2,4-diones

Julia Beneke
Lehrstuhl für Organische Chemie, Universität Bayreuth, Universitätsstraße 30, 95440 Bayreuth, Germany   Fax: +49(921)552671   Email: Rainer.Schobert@uni-bayreuth.de
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Rainer Schobert*
Lehrstuhl für Organische Chemie, Universität Bayreuth, Universitätsstraße 30, 95440 Bayreuth, Germany   Fax: +49(921)552671   Email: Rainer.Schobert@uni-bayreuth.de
› Author Affiliations
Further Information

Publication History

Received: 30 November 2012

Accepted after revision: 04 February 2013

Publication Date:
14 February 2013 (online)


Abstract

β-Lactones were prepared by irradiation of 3-diazodihydrofuran-2,4-diones via Wolff rearrangement proceeding with retention of the configuration of the migrating carbon atom. In the presence of alcohols or thiols, but not amines, the corresponding 3-(alkoxycarbonyl)- or 3-[(alkylsulfanyl)carbonyl]-β-lactones were obtained. 5-Alkyl-3-diazodihydrofuran-2,4-diones gave exclusively trans-3,4-disubstituted β-lactones.

Supporting Information

 
  • References

  • 1 Yang HW, Romo D. Tetrahedron 1999; 55: 6403
  • 2 Pommier A, Pons JM. Synthesis 1993; 441
  • 3 Pommier A, Pons JM. Synthesis 1995; 729
  • 4 Lowe C, Vederas J. Org. Prep. Proced. Int. 1995; 27: 305
  • 5 Böttcher T, Sieber SA. Angew. Chem. Int. Ed. 2008; 47: 4600
  • 6 Tomoda H, Kumagai H, Tanaka H, Omura S. J. Antibiot. (Tokyo) 1993; 46: 872
  • 7 Hadváry P, Sidler W, Meister W, Vetter W, Wolfer H. J. Biol. Chem. 1991; 266: 2021
  • 8 Stork G, Szarjewski RP. J. Am. Chem. Soc. 1974; 437: 5787
  • 9 Regitz M, Stadler D, Schwall H, Liedhegener A, Geelhaar HJ, Menz F, Hocker J, Rüter J, Anschütz W. Angew. Chem. 1967; 79: 786
    • 10a Schobert R, Stehle R, Walter H. Tetrahedron 2008; 64: 9401
    • 10b Löffler J, Schobert R. J. Chem. Soc., Perkin Trans. 1 1996; 2799
  • 11 Newman MS, Beal III PF. J. Am. Chem. Soc. 1950; 72: 5163
  • 12 Effenberger F, Syed J. Tetrahedron: Asymmetry 1998; 9: 817
  • 13 Brandaenge S, Flodman L, Norberg Å, Boll PM. J. Org. Chem. 1984; 49: 927