77927-89-0Relevant academic research and scientific papers
-WITTIG REARRANGEMENT OF ALLYLIC GLYCOLATE ESTERS VIA BORON AND TIN ENOLATES
Oh, Taeboem,Wrobel, Zbigniew,Rubenstein, Steven M.
, p. 4647 - 4650 (1991)
Wittig rearrangement of allylic glycolate esters via boron and tin enolates gave diastereoselectivities as high as 99.5 : 0.5.Tin enolates were more stereoselective than boron enolates.
Non-carbonyl-stabilized metallocarbenoids in synthesis: The development of a tandem rhodium-catalyzed bamford-stevens/thermal aliphatic claisen rearrangement sequence
May, Jeremy A.,Stoltz, Brian M.
, p. 12426 - 12427 (2007/10/03)
A tandem rhodium-catalyzed Bamford-Stevens/Claisen rearrangement is presented. The tandem reaction uses Eschenmoser hydrazones for the in situ generation of non-carbonyl-stabilized diazo alkanes, which are presumably intercepted by Rh(II) catalysts to induce a 1,2-hydride migration. This sequence provides high levels of stereocontrol for the generation of simple acyclic (Z)-enol ethers. These enol ethers undergo either thermal or Lewis acid accelerated Claisen rearrangements to provide products of high diastereopurity. Also presented are cascade reactions, wherein a third chemical step occurs after the initial tandem sequence (i.e., Bamford-Stevens/Claisen/ene and Bamford-Stevens/Claisen/Cope). Copyright
THE WITTIG REARRANGEMENT OF 2-ALKENYLOXYACETIC ACIDS AND ITS APPLICATIONS TO THE STEREOCONTROLLED SYNTHESIS OF β,γ-UNSATURATED ALDEHYDES AND CONJUGATED DIENOIC ACIDS
Nakai, Takeshi,Mikami, Koichi,Taya, Shiro,Kimura, Yasuhiro,Mimura, Tetsuya
, p. 69 - 72 (2007/10/02)
Dianions generated from 2-alkenyloxyacetic acids readily undergo the sigmatropic rearrangement which can constitute the versatile synthetic sequences for the stereocontrolled synthesis of β,γ-unsaturated aldehydes and conjugated dienoic acids.
