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Passerini reactions for the efficient synthesis of 3,3-disubstituted oxetanes
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Beasley, B., Clarkson, Guy J. and Shipman, Michael. (2012) Passerini reactions for the efficient synthesis of 3,3-disubstituted oxetanes. Tetrahedron Letters, Vol.3 (No.24). pp. 2951-2953. ISSN 0040-4039
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2012.03.065
Abstract
Three-component reactions of oxetan-3-ones with isocyanides and carboxylic acids produce 3,3-disubstituted oxetanes in good yields. Good levels of diastereocontrol (dr = 4:1) can be achieved in these Passerini reactions when the oxetane nucleus possesses a bulky cyclohexyl substituent at C–2. The (2S∗,3R∗)-stereochemistry of the major diastereomer was confirmed by X-ray crystallography after ester hydrolysis, and a possible mechanism to account for the diastereofacial selectivity is presented.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Journal or Publication Title: | Tetrahedron Letters |
| Publisher: | Elsevier |
| ISSN: | 0040-4039 |
| Date: | 13 June 2012 |
| Volume: | Vol.3 |
| Number: | No.24 |
| Page Range: | pp. 2951-2953 |
| Identification Number: | 10.1016/j.tetlet.2012.03.065 |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| URI: | http://wrap.warwick.ac.uk/id/eprint/47934 |
Data sourced from Thomson Reuters' Web of Knowledge
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