Sulfoxide-directed desymmetrisation of cyclohexa-1,4-dienes

The cyclisation of enolate anions onto cyclohexadienes can be controlled by the use of a chiral sulfoxide. Cyclohexa-2,5-dien-1-ylmethanol derivatives have been subjected to a short sequence featuring esterification to introduce a malonate side-chain, oxidation of the doubly allylic position and ste...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 26; pp. 4561 - 4564
Main Authors Elliott, Mark C., El Sayed, Nahed Nasser Eid, Ooi, Li-ling
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.06.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIASTEREOSELECTION
ASYMMETRIC-SYNTHESIS
INTRAMOLECULAR CONJUGATE ADDITION
SELECTIVE RADICAL CYCLIZATIONS
STRATEGY
HYDROGEN-PEROXIDE
STEREOSELECTIVE-SYNTHESIS
QUATERNARY CARBON
DESYMMETRIZATION
ALKALOIDS
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Summary:The cyclisation of enolate anions onto cyclohexadienes can be controlled by the use of a chiral sulfoxide. Cyclohexa-2,5-dien-1-ylmethanol derivatives have been subjected to a short sequence featuring esterification to introduce a malonate side-chain, oxidation of the doubly allylic position and stereoselective cyclisation. When used in conjunction with a chiral sulfoxide, the cyclisation is diastereoselective (2:1) favouring one of the diastereotopic double-bonds.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.04.138