ChemInform Abstract: Palladium(0)-Catalyzed Rearrangements of Allylic Sulfoximines to Allyl Sulfinimidic Acid Esters and Optically Active N-Cbz Protected γ-Amino-enones.

✍ Scribed by S. G. PYNE; D. M. DAVID; Z. DONG

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199905096

✦ Synopsis

1999 sulfenic acids, sulfinic acids sulfenic acids, sulfinic acids (benzene compounds) Q 0570

05 -096

Palladium(0)-Catalyzed Rearrangements of Allylic Sulfoximines to Allyl Sulfinimidic Acid Esters and Optically Active N-Cbz Protected γ-Amino-enones.

-Attempted asymmetric rearrangement of sulfoximes (I) to α-keto-allylic sulfinamides gives unexpectedly the racemic benzenesulfinimidic acid esters (II). On the other hand, analogous rearrangement of the N-Cbz protected starting materials (III) gives optically active γ-amino enones (IV) after solvolytic work-up. -(