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.
α-Carboxy-β-lactones from Photoinduced Ring Contraction of 3-Diazodihydrofuran-2,4-diones. -In the presence of alcohols or thiols, formation of β-lactones via Wolff rearrangement takes place. Interestingly, optically active 5-monoalkyl-substituted substrates give trans-3,4-disubstituted products exclusively with retention of configuration. -(BENEKE, J.; SCHOBERT*, R.; Synthesis 45 (2013) 6, 773-776, http://dx.doi.org/10.1055/s-0032-1316860 ; Lehrstuhl Org. Chem., Univ. Bayreuth, D-95447 Bayreuth, Germany; Eng.) -Mais 25-090
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