The imidazolylsulfonate group has been found to be a versatile leaving group in the intramolecular cyclization of p-methoxyphenyl amides and related derivatives of N-substituted L-serine to give the corresponding β-lactams.
1,6‐Additions to 3‐Methyl‐5‐methylidene‐2(5H)‐furanone Derivatives
The anions of thiophenol, methyl malonate and malononitrile react with 3‐methyl‐5,6‐dihydro‐2 (4H)‐benzofuranone (1c) by the formation of the corresponding 1,6‐addition products cis‐5c (63%), trans‐6 (42%) and trans‐7 (76%), respectively. Likewise, the reaction of 3‐methyl‐5‐methylidene‐2 (5H)‐furanone (1b) with thiophenol yields the 1,6‐addition product 5b (66%), and with the sodium salt of methyl aceto‐acetate the 1,6‐addition product 8 (11%) and the dispiro‐dilactone 9 (39%).
Stereoselective Hydride Reduction of Tetronic Acid Derivatives. Synthesis of Branched-Chain TetrofuranosesSummary The 3-methoxymethyl derivatives of 2-methyl-~, L-threofuranose (10a) and 2-deoxy-2-methyl-~, L-erythrofuranose (1 1 a) are prepared starting from 2-methyltetronic acid (1). The key step is the stereoselective reduction of the 3-0x0-function of 2-chloro-2-methyl-3-oxo-y-butyrolacton (2) by sodiumborohydride, which proceeds predominantly anti with respect to the C, C1-bond. The configuration of the reduction products has been established by 'H-and '3C-NMR.-spectroscopy.
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