1,3-Rearrangement of ketene-N,O-acetals

✍ Scribed by Tatsuo Suzuki; Masaharu Inui; Seijiro Hosokawa; Susumu Kobayashi

• Book ID: 104253415
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 194 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00610-5

✦ Synopsis

Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.