Journal article
A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds
Journal of Organic Chemistry, Vol.66(23), pp.7811-7817
2001
Abstract
Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)-tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
Details
- Title
- A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds
- Authors
- A McCluskey (Author) - University of NewcastleI W Muderawan (Author) - University of NewcastleMuntari Young (Author) - University of NewcastleDavid James Young (Author) - Griffith University
- Publication details
- Journal of Organic Chemistry, Vol.66(23), pp.7811-7817
- Publisher
- American Chemical Society
- Date published
- 2001
- DOI
- 10.1021/jo015904x
- ISSN
- 0022-3263
- Organisation Unit
- University of the Sunshine Coast, Queensland
- Language
- English
- Record Identifier
- 99449292502621
- Output Type
- Journal article
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- Domestic collaboration
- Web Of Science research areas
- Chemistry, Organic
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Source: InCites