[1,3] Sigmatropic rearrangement of ketene silyl acetals derived from benzyl α-substituted propanoates

✍ Scribed by Isamu Shiina; Hiroshi Nagasue

• Book ID: 104251561
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 122 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01168-1

✦ Synopsis

A novel [1,3] sigmatropic rearrangement of ketene silyl acetals derived from benzyl a-substituted propanoates is developed. The reaction of ketene silyl acetal derived from optically active 1-phenylethyl 2-methylpropanoate mainly proceeds with the retention of chirality at the benzyl position to give the corresponding optically active silyl ester under thermodynamic conditions.