Nucleophilic acylation of esters by acid chlorides mediated by samarium diiodide: Formation and use of samarium enediolates.

DOI: 10.1016/S0040-4039(97)01727-9

Source and publish data:

Tetrahedron Letters p. 7183 - 7186 (1997)

Update date:2022-08-03

Topics: Reduction Carbonyl group Organic synthesis Esters Oxidation state Acid chlorides Alkoxy group reactive intermediate Radical intermediate Acyl group Resonance stabilization

Authors:

Machrouhi, Fouzia

Namy, Jean-Louis

Kagan, Henri B.

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Article abstract of DOI:10.1016/S0040-4039(97)01727-9

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.

Full text of DOI:10.1016/S0040-4039(97)01727-9

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