ChemInform Abstract: Asymmetric Dipolar Cycloadditions of Me3SiCHN2. Synthesis of a Novel Class of Amino Acids: Azaprolines.

✍ Scribed by M. R. MISH; F. M. GUERRA; E. M. CARREIRA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 38 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199801218

✦ Synopsis

Asymmetric Dipolar Cycloadditions of Me 3 SiCHN 2 . Synthesis of a Novel Class of Amino Acids: Azaprolines.

-The novel diastereoselective dipolar cycloaddition of (II) with the chiral, camphor-sultam-derived acrylates (I) provides access to optically active ∆ 2 -pyrazolines such as (III). These compounds represent novel substituted proline analogues, which are not previously prepared. The utility of these azaproline derivatives is demonstrated by their reactions showing reduction, chemoselective protection, auxiliary removal and peptide bond formation.