Dephosphonylation of alpha-fully substituted beta-keto phosphonates with LiAlH4; Regioselective alkylation of ketones employing phosphonate as a temporary activating group
Alkylation of beta-keto phosphonates is performed by treatment of beta-keto phosphonates with n-BuLi, followed by addition of alkyl halides. The acquired a fully substituted beta-keto phosphonates are dephosphonylated by treatment of the lithium enolates with LiAlH4, followed by quenching with aqueous H2SO4 solution. This whole procedure represents a new route to regioselective alkylation of ketones. (C) 1997 Elsevier Science Ltd.