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Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: Samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates

Author:
Soto, Martín, Soengas, Raquel G., Silva, Artur M.S., Gotor-Fernández, Vicente, Rodríguez-Solla, Humberto
Source:
Tetrahedron 2018 v.74 no.38 pp. 5475-5480
ISSN:
0040-4020
Subject:
acetates, acetylation, aldehydes, chemical structure, cross-coupling reactions, halides, organic halogen compounds, samarium, silanes, stereoselectivity
Abstract:
A general and highly selective method for the synthesis of carbohydrate-derived (Z)-vinyl halides and silanes is described. This reaction takes place through a β-elimination process of sugar-derived α-halomethylcarbinol acetates promoted by samarium diiodide. Starting materials have been easily prepared in two steps consisting in an initial addition of halomethyllithium compounds to the corresponding galactose-derived aldehyde, followed by acetylation. A mechanism that explains both the formation of (Z)-vinyl derivatives and its selectivity is proposed. Finally, the synthetic usefulness of these compounds has been applied in cross-coupling reactions with ethynyl benzene towards the formation of selected enyne derivatives.
Agid:
6130859