Ene reaction of the active XCN− and XCO group with ketones. A novel synthesis of X-oxo-α-amino- and X-oxo-oα-hydroxy-acids.

✍ Scribed by Osman Achmatowicz Jr.; Marek Pietraszkiewicz

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 266 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82946-4

✦ Synopsis

Thermal reaction of butyl N-(p-toluenesulphonyl)iminoacetate and diethyl mesoxalate with ketones leads to the derivatives of f-0x0-d-amino-acids and c-oxo-o(-hydroxy--acids, respectively. 1 b.p's or m.p's and ZR spectra are collected in Table 1 and H NMR data in Table 2. All new compounds gave correct C ,H, N elemental analyses.

TABLE 1 Yield M-p. ("C) IRa: Smax(cm-') Compound (%) (B.p. [OC/Tord) NH(OH) C=O(ester) C=O(ketone) SO,, 3a 81 -b-z? 89 gc 78 ?.