ChemInform Abstract: Selective Synthesis of cis-2-Vinyl-3-alkylaziridines and 3-Pyrrolines from Common Intermediates (Z)-4-N-Arylsulfonylaminoalk-2-en-1-ols.

✍ Scribed by Kiyonori Ishii; Hiroaki Ohno; Yoshiji Takemoto; Eriko Osawa; Yumiko Yamaoka; Nobutaka Fujii; Toshiro Ibuka

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199946126

✦ Synopsis

Selective Synthesis of cis-2-Vinyl-3-alkylaziridines and 3-Pyrrolines from Common Intermediates (Z)-4-N-Arylsulfonylaminoalk-2-en-1ols.

-Both the title aziridines and pyrrolines are conveniently available from Z-aminoalkenols (I) by properly choosing the reaction conditions. Thus, palladium-catalyzed cyclization of the corresponding carbonates (III) affords the thermodynamically more stable cis-2-vinylaziridines (IV) in good yields and excellent diastereoselectivity. In contrast, base-mediated cyclization of the mesylates (VI) gives pyrrolines (VII) in high yields as the sole reaction products. The latter sequence can be successfully applied to the synthesis of biologically important 3,4-dehydroproline (X). -(ISHII, KIYONORI; OHNO, HIROAKI;