A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to carbonyl compounds

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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