68877-57-6Relevant academic research and scientific papers
Asymmetric addition of alkoxy ethynyl anion to chiral N-sulfinyl imines
Verrier, Charlie,Carret, Sebastien,Poisson, Jean-Francois
, p. 5122 - 5125 (2012)
The addition of lithiated ynol ethers to chiral N-sulfinyl imines proceeds in high yield and diastereoselectivity. The selectivity is completely reversed by the addition of boron trifluoride. These alkoxypropargyl sulfinamides can be reduced to afford eno
Nickel-catalyzed [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: Application to selective three-component reaction with 1,3-diynes
Yamasaki, Ryu,Terashima, Natsuki,Sotome, Ikuo,Komagawa, Shunsuke,Saito, Shinichi
supporting information; experimental part, p. 480 - 483 (2010/03/25)
(Chemical Equation Presented) Heteroatom-substituted alkynes such as ynol ethers and ynamines turned out to be decent substrates for the Nicatalyzed [3 + 2 + 2] cocyclization of ethyl cyclopropylideneacetate (1). The three-component cocyclization of 1, 1,
Total synthesis of the anticancer natural product OSW-1
Yu, Wensheng,Jin, Zhendong
, p. 6576 - 6583 (2007/10/03)
The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3β-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of α-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of α-halo vinyl ether chemistry developed in our laboratories.
Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. the Bridged Mode (β-Tether)
Denmark, Scott E.,Dixon, Julie A.
, p. 6167 - 6177 (2007/10/03)
A new variation of the tandem inter [4 + 2]/intra [3 + 2] cycloaddition of nitroalkenes has been developed. This method involves the Lewis acid-promoted [4 + 2] cycloaddition of nitro olefins 12 with 1-alkoxy-1,4-dienes 3. The resulting nitronates 13, bearing a C(5) tethered dipolarophile, undergo thermal, intramolecular [3 + 2] cycloaddition to afford stable tricyclic nitroso acetals 14, which can be subsequently reduced to unveil a new carbocycle 16, Thus, in three steps, highly functionalized aminocyclopentanes can be stereoselectively constructed in high yield.
The photochemistry of acetylenic ethers. A novel carbon-oxygen to carbon-carbon bond conversion
Smith, Bradley A.,Callinan, Andrew J.,Swenton, John S.
, p. 2283 - 2286 (2007/10/02)
Irradiation of acetylenic ethers in methanol gives homologated esters via a formal [1,3]-oxygen-to-carbon migration involving a ketene intermediate.
