The reaction of trialkylstannylmethyllithium with α,β-epoxy ketones. A preparative method of β, γ-unsaturated ketones by homologation of α, gb-unsaturated ketones
✍ Scribed by Tadashi Sato; Toshihiro Kikuchi; Norio Sootome; Eigoro Murayama
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 224 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
a,@-Epoxy ketones 2_, upon treatment with two equivalents of trialkylstannylmethyllithium 1, afforded cyclopropanols 2 as a single product in acyclic system, and a mixture of cyclopropanols 2 and methylene 1,2-diols 2 in cyclic system. Under acidic conditions, the cyclopropanols gave p,y-unsaturated ketones 5 in good yields.
📜 SIMILAR VOLUMES
Treatment of c~-silyl-cc,[~-unsaturated enones, readily preparable as regio-and stereodefined compounds in high yields, with either 2 equiv, oflCl or one equiv, each oflC1 and A1C13 provides the corresponding cc-iodo-a,[3unsaturated enones in high yields.
The reaction of a,fMuwsturated aldehydes and ketones with organotin hydrides have been studied intensively by Kuivils and Beumel 1,2 and by Valade and Pereyre 394. Where88 in the first reports on thin subject '9295 selective reduotion of the oarbonyl function (1) wae the only reaction observed, it h