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

Elliott, Mark Christopher, El Sayed, Nahed Nasser and Ooi, Liling 2007. Sulfoxide-directed desymmetrisation of cyclohexa-1,4-dienes. Tetrahedron Letters 48 (26) , pp. 4561-4564. 10.1016/j.tetlet.2007.04.138

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Last Modified: 12 Oct 2017 04:04

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