111832-37-2Relevant articles and documents
Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
Lambert, Tristan H.,Steiniger, Keri A.
supporting information, p. 8013 - 8017 (2021/10/25)
The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.
A new synthesis of β-keto phosphonate from aryl epoxysulfones and dialkyl hydrogen phosphite
Koh, Young Joo,Oh, Dong Yung
, p. 2147 - 2148 (2007/10/02)
Reaction of α-subtituted arylsulfonyl epoxide with diethyl phosphite sodium salt gave β-keto phosphonate in good yield.
A stereocontrolled approach to electrophilic epoxides
Meth-Cohn, Otto,Moore, Clive,Taljaard, Heinrich C.
, p. 2663 - 2674 (2007/10/02)
Lithium t-butyl hydroperoxide (easily generated by addition of an alkyl-lithium to anhydrous t-butyl hydroperoxide in THF solution) is a powerful reagent for the epoxidation of electrophilic alkenes at -20 to 0 °C under full stereocontrol. Thus αβ-unsaturated esters, sulphones, sulphoximines, and amides are readily epoxidised with complete regio- and stereo-specificity and with considerable chiroselectivity (20-100%) when appropriate chiral auxiliaries such as menthyl, 8-phenylmenthyl, or a camphor-sulphonamide derivative are used. Asymmetric αβ-unsaturated sulphoximines undergo epoxidation with 100% diastereoselectivity. The only exceptions to stereocontrol noted are heavily substituted maleate esters such as di-t-butyl maleate. The αβ-epoxy amides are shown to be valuable sources of the corresponding epoxy ketones by treatment with an organolithium, allowing a stereo- and chemoselective entry in high yield to these useful intermediates.
