Dephosphonylation of α-fully substituted β-keto phosphonates with LiAlH4; regioselective alkylation of ketones employing phosphonate as a temporary activating group

✍ Scribed by Shi Yong Lee; Jong Eoun Hong; Won Bum Jang; Dong Young Oh

• Book ID: 104257333
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 186 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00975-1

✦ Synopsis

Alkylation of [5-keto phosphonates is performed by teatment of 15-keto phosphonates with n-BuLi, followed by addition of alkyl halides. The acquired c~fully substituted 13-keto phosphonates are dephosphonylated by treatment of the lithium enolates with LiAIH4, followed by quenching with aqueous H2SO4 solution. This whole procedure represents a new route to regioselective alkylation of ketones.