Copper (I) mediated highly diastereoselective conjugate addition of Grignard reagents to functionalised 6-membered ring cycloalkenols. Synthesis of cyclohexanes derivatives substituted on three contiguous atoms

Copper catalysed conjugate addition of Grignard reagents to 2-silyloxycyclohexene carboxylates in the presence of an excess chlorotrimethylsilane, leads diastereoselectively to related (anti) (Z) silylketene acetals. Subsequent hydrolysis and desilylation afford 2-hydroxycyclohexane carboxylates in...

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Bibliographic Details
Published in:Tetrahedron letters 1999-01, Vol.40 (5), p.871-874
Main Authors: Dambrin, Valéry, Villiéras, Monique, Lebreton, Jacques, Toupet, Loïc, Amri, Hassen, Villiéras, Jean
Format: Article
Language:English
Subjects:
2-Hydroxycyclohexane carboxylates
2-Silyloxycyclohexene carboxylates
Conjugate Addition
Copper catalysed Grignard reactions
Diastereoselectivity
ketene acetals
Michaël reactions
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Summary:Copper catalysed conjugate addition of Grignard reagents to 2-silyloxycyclohexene carboxylates in the presence of an excess chlorotrimethylsilane, leads diastereoselectively to related (anti) (Z) silylketene acetals. Subsequent hydrolysis and desilylation afford 2-hydroxycyclohexane carboxylates in high yields and diastereoselectivities. Copper (I) mediated conjugate addition of Grignard reagent to 2-silyloxycyclohexene carboxylates leads after deprotection to related syn-anti cyclohexanols in high yields and selectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02543-X