PHOSPHORYL FUNCTIONALIZED BISHOMOALLYL ALCOHOLS BY RING-OPENING OF EPOXIDES WITH LITHIATED ALLYLDIPHENYLPHOSPHANE OXIDE

Authors
ERGUDEN JK SCHAUMANN E
Citation
Jk. Erguden et E. Schaumann, PHOSPHORYL FUNCTIONALIZED BISHOMOALLYL ALCOHOLS BY RING-OPENING OF EPOXIDES WITH LITHIATED ALLYLDIPHENYLPHOSPHANE OXIDE, Synthesis, (6), 1996, pp. 707
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
6
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):6<707:PFBABR>2.0.ZU;2-#
Abstract
Epoxides are attacked by the lithiated anion of allyldiphenylphosphane oxide in 1,2-dimethoxyethane as solvent in a boron trifluoride-diethy l ether complex promoted ring opening reaction to afford a mixture of regioisomeric bishomoallyl alcohols (alpha- and gamma-attack of the nu cleophile) in good overall yields. When toluene is used as reaction me dium a pronounced preference for gamma-attack of the anion is observed .