- Title
- A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to carbonyl compounds
- Creator
- McCluskey, Adam; Muderawan, I. Wayan; Muntari,; Young, David J.
- Relation
- Journal of Organic Chemistry Vol. 66, Issue 23, p. 7811-7817
- Publisher Link
- http://dx.doi.org/10.1021/jo015904x
- Publisher
- American Chemical Society
- Resource Type
- journal article
- Date
- 2001
- Description
- 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.
- Subject
- stannanes; carbonyl compounds
- Identifier
- uon:1334
- Identifier
- http://hdl.handle.net/1959.13/27050
- Identifier
- ISSN:0022-3263
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