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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.53 (No.24). pp. 2951-2953. doi:10.1016/j.tetlet.2012.03.065 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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Tetrahedron Letters | ||||
Publisher: | Elsevier | ||||
ISSN: | 0040-4039 | ||||
Official Date: | 13 June 2012 | ||||
Dates: |
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Volume: | Vol.53 | ||||
Number: | No.24 | ||||
Page Range: | pp. 2951-2953 | ||||
DOI: | 10.1016/j.tetlet.2012.03.065 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
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