Catalytic allylation of hydrates of α-keto aldehydes and glyoxylates with allyltrimethylsilane using non-fluorine-containing sulfonic acids as catalysts

✍ Scribed by Ming Wen Wang; Yong Jun Chen; Dong Wang

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 129 KB
• Volume: 12
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.1081

✦ Synopsis

Abstract

Methanesulfonic acid, aromatic sulfonic acids, and 10‐camphorsulfonic acid have been used as catalysts in allylation of hydrates of α‐keto aldehydes 1a–d and glyoxylates 1e–f with allyltrimethylsilane 2 to afford the corresponding homoallylic alcohols 4a–e in good yields. Two plausible mechanisms of sulfonic acid–catalyzed allylation reactions with an allysilane are discussed. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:534–538, 2001