99309-95-2Relevant academic research and scientific papers
Nucleophilic acylation of esters by acid chlorides mediated by samarium diiodide: Formation and use of samarium enediolates.
Machrouhi, Fouzia,Namy, Jean-Louis,Kagan, Henri B.
, p. 7183 - 7186 (1997)
Acid chlorides react with esters in the presence of samarium diiodide and catalytic amounts of NiI2 to afford samarium enediolates which can further react with electrophiles such as water or aldehydes to give respectively α-ketols or α-dihydroxyketones.
Tandem Alkylation-Reduction. Highly Stereoselective Synthesis of (E)-1-Hydroxymethyl Methyl Propenyl Ethers from Aldehydes Using 1-Lithio-1-methoxyallene
Weiberth, Franz J.,Hall, Stan S.
, p. 5308 - 5314 (2007/10/02)
Tandem alkylation-reduction of a series of aldehydes, by alkylating with 1-lithio-1-methoxyallene followed by reducing with lithium-ammonia, regiospecifically and highly stereoselectively affords the 1-hydroxymethyl methyl propenyl ether in which the alkene geometry is exclusively E.Aldehydes that have been subjected to this convenient procedure include aromatic, aliphatic, and heterocyclic aldehydes.Subsequent hydrolysis, in the aromatic and aliphatic cases, affords the corresponding α-hydroxy ethyl ketones.The stereochemistry of the propenyl ethers was established by 13C NMR spectroscopy.A mechanism for the selective reduction of the methoxyallene system is proposed.
