Inversion of the Configuration of Secondary Alcohols via Isourea Ethers Prepared in situ

✍ Scribed by Dr. Johannes Kaulen

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: English
• Weight: 240 KB
• Volume: 26
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198707731

✦ Synopsis

I H. 4-H), 2.55 (m, 4 H, 2.3-H; 5(2,3)= 15.8 Hz).-The other reactions of 5 shown in Scheme 2 were carried out analogously (no optimization). In each case, the reaction products were converted into the methyl esters with CH,OH/HCI. The characterization and quantification of the ester was carried out by GC or by GC-MS (reference compounds).

[9] B. Bogdanovic, M. Kroner, G. Wilke, Justus Liebigs Ann. Chem. 699

(1966) I .

temperature IS]. Solid, high-melting alcohols were allowed to stir in a small amount of anhydrous dioxane for 3 d at 40-50°C.

3: Crude 2 (0.5 mol) was dissolved in 200 mL of dry solvent (preferably toluene) and the carboxylic acid (0.6 mol, preferably formic acid) was added to the stirred solution at room temperature. The resulting mixture was heated at