ChemInform Abstract: 4-Alkyl-2-trichloromethyloxazolidin-5-ones: Valuable Precursors to Enantiomerically Pure C- and N-Protected α-Alkyl Prolines.

✍ Scribed by Harry Wang; Juris P. Germanas

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199920174

✦ Synopsis

Lithiation of the L-proline derived 2-trichloromethyloxazolidin-5-one (I) and following reaction with alkyl halides yields the 4-substituted derivatives (III) with excellent diastereoselectivity. They can be easily cleaved to the proline esters (V). Hydrolysis or methanolysis of the N,O-acetal function is achieved under acidic conditions.