67921-28-2Relevant academic research and scientific papers
The first radical method for the introduction of an ethynyl group using a silicon tether and its application to the synthesis of 2′-deoxy-2′-C-ethynylnucleosides
Sukeda, Makoto,Ichikawa, Satoshi,Matsuda, Akira,Shuto, Satoshi
, p. 3465 - 3475 (2003)
A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3
Gold-catalyzed rearrangement of allylic oxonium ylides: Efficient synthesis of highly functionalized dihydrofuran-3-ones
Fu, Junkai,Shang, Hai,Wang, Zhaofeng,Chang, Le,Shao, Wenbing,Yang, Zhen,Tang, Yefeng
supporting information, p. 4198 - 4202 (2013/05/08)
"Diazo" not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3-sigmatropic rearrangement, or a stepwise 1,4-allyl migration followed by a Claisen rearrangement (see scheme). Copyright
Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides
Aurrecoechea, José M.,Gil, Jesús H.,López, Beatriz
, p. 7111 - 7121 (2007/10/03)
The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (α or β, respectively).
