DEPHOSPHONYLATION OF ALPHA-FULLY SUBSTITUTED BETA-KETO PHOSPHONATES WITH LIALH4 - REGIOSELECTIVE ALKYLATION OF KETONES EMPLOYING PHOSPHONATE AS A TEMPORARY ACTIVATING GROUP

Authors
LEE SY HONG JE JANG WB OH DY
Citation
Sy. Lee et al., DEPHOSPHONYLATION OF ALPHA-FULLY SUBSTITUTED BETA-KETO PHOSPHONATES WITH LIALH4 - REGIOSELECTIVE ALKYLATION OF KETONES EMPLOYING PHOSPHONATE AS A TEMPORARY ACTIVATING GROUP, Tetrahedron letters, 38(26), 1997, pp. 4567-4570
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
26
Year of publication
1997
Pages
4567 - 4570
Database
ISI
SICI code
0040-4039(1997)38:26<4567:DOASBP>2.0.ZU;2-Y
Abstract
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 dephospho nylated 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 Elsevie r Science Ltd.