97537-58-1Relevant academic research and scientific papers
Diversity-oriented stereoselective synthesis of β,γ-disubstituted tert-homoallylic alcohols
Takeda, Takeshi,Amarume, Sota,Sekioka, Ippei,Tsubouchi, Akira
, p. 1150 - 1153 (2015)
The successive treatment of β-(trimethylsilyl)allyl phenyl sulfides with titanocene(II)-1-butene complex and ketones produced tertiary γ-(trimethylsilyl)homoallylic alcohols with good anti-selectivity, which reacted with a variety of organic halides in th
Preparation of methylenedifluorocyclopropanes via cyclopropyl anion promoted β-elimination
Shibuya, Akira,Okada, Midori,Nakamura, Yuko,Kibashi, Mie,Horikawa, Hiroaki,Taguchi, Takeo
, p. 10325 - 10340 (2007/10/03)
Preparation of methylenedifluorocyclopropanes 2 through the β- elimination reaction promoted by difluorocyclopropyl anion formed by cleavage of C-Si bond with TBAF is described. Base-catalyzed isomerization of 2 to difluorocyclopropene 11 shows the latter structure thermodynamically more stable in contrast to non-fluorinated cases. Application of this method to the synthesis of methylenedifluorocyclopropylglycine (F2MCPG) derivative 17 is also presented.
Generation and trapping of allene oxides: An approach to chiral, nonracemic α-alkoxyketones
Shipman, Michael,Thorpe, Heidi R.,Clemens, Ian R.
, p. 14265 - 14282 (2007/10/03)
Epoxy mesylates 5 react with a variety of sodium alkoxides to produce the corresponding α-alkoxyketones in good yields. Evidence is presented for the involvement of transient allene oxides in these reactions. Enantiomerically enriched epoxy mesylates (2R,3S)-5a-c were prepared using the Sharpless asymmetric epoxidation reaction as the key step. These precursors rearrange to α-alkoxyketones without significant racemisation under modified reaction conditions (ROK, 18-crown-6, THF, -78°C). The reactions are shown to proceed with stereochemical inversion at the epoxide centre.
