Simple and efficient stereocontrol of radical allylations of β-hydroxy esters

Highly stereoselective radical allylations of non-protected β-hydroxy esters have been achieved after formation of chelated aluminum alkoxides upon treatment with MeAlR 2. This approach combines very high selectivities, excellent reproductibility and simplicity of the manipulations. Interestingly, d...

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Bibliographic Details
Published in:Tetrahedron letters 1996-08, Vol.37 (35), p.6335-6338
Main Authors: Gerster, Michèle, Audergon, Laurent, Moufid, Nadira, Renaud, Philippe
Format: Article
Language:English
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Summary:Highly stereoselective radical allylations of non-protected β-hydroxy esters have been achieved after formation of chelated aluminum alkoxides upon treatment with MeAlR 2. This approach combines very high selectivities, excellent reproductibility and simplicity of the manipulations. Interestingly, diethyl malate is allylated after treatment with 1.1 equiv. of MAD to the threo (syn) isomer with almost complete diastereoselectivity (> 95% ds), this stereochemical outcome is opposite to the one observed in the well-known alkylation of the corresponding enolate. Highly stereoselective radical allylations of nonprotected β-hydroxy esters have been achieved after formation of chelated aluminum alkoxides upon treatment with MeAlR 2.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01396-2