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

被引：34

作者：

McCluskey, A

Muderawan, IW

Muntari

Young, DJ

机构：

[1] Univ Newcastle, Sch Biol & Chem Sci, Callaghan, NSW 2308, Australia

[2] Griffith Univ, Fac Sci & Technol, Brisbane, Qld 4111, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 23期

关键词：

D O I：

10.1021/jo015904x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：7811 / 7817

页数：7

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