Selective Conversion of Enol Ethers into Alcohols in the Presence of Alkenes Using Hg(OAc)2-NaBH4

Abstract

Alkyl enol ethers derived from aldehydes undergo selective oxymercuration-demercuration with aqueous Hg(OAc) 2 -NaBH 4 in the presence of an alkene in good to excellent yield. This method allows the survival of mono-, trans and cis di-, and tri-substituted alkenes as well as cyclic alkenes.

A Facile Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

“…Compound 8 can be converted into a Grignard reagent, and then this was coupled with allyl bromide under Li 2 CuCl 4 catalysis to form 9 in 66% yield [ 15 , 16 ]. Afterwards, the THP group was removed in methanol in the presence of 4-methyl-benzenesulfonic acid [ 17 , 18 ]. Compound 11 was produced in 90% yield after 10 was subjected to a Corey-Fuji protocol.…”

Synthesis of γ,δ-Unsaturated-β-keto Lactones via Sequential Cross Metathesis−Lactonization: A Facile Entry to Macrolide Antibiotic (−)-A26771B

“…In addition to purchasable 9-decen-1-ol ( 1a ), the long-chain alcohols 1b − d were favored as adequate substrates because they can be easily derived from commercially available compounds (Scheme ). While dodecenol 1b and tetradecenol 1c could be prepared according to literature procedures, the direct conversion of 11-bromo-1-undecanol ( 8 ) with allylmagnesium bromide in the presence of CuI produced significant amounts of byproduct. However, refluxing the corresponding THP ether with excess allylmagnesium chloride in THF gave the known tetradecenol 1d in 67% overall yield after deprotection.…”