220416-57-9Relevant academic research and scientific papers
Thermal [2 + 2]-Cycloaddition of Ketenes with Chiral Enol Ethers: Route to Densely Substituted Cyclobutanones
Rullière, Pauline,Grisel, Julien,Poittevin, Clément,Cividino, Pascale,Carret, Sébastien,Poisson, Jean-Fran?ois
supporting information, p. 2824 - 2827 (2016/07/06)
Access to chiral polysubstituted cyclobutanones by [2 + 2]-cycloaddition of ketenes with chiral acyclic enol ethers is reported. A wide variety of easily accessible di- and monosubstituted ketenes were found to react with a very high degree of stereoselec
Asymmetric synthesis of cyclobutanones: Synthesis of cyclobut-G
Darses, Benjamin,Greene, Andrew E.,Poisson, Jean-Francois
experimental part, p. 1710 - 1721 (2012/04/23)
A simple, efficient, and stereoselective approach has been developed for obtaining chiral cis- and trans-disubstituted cyclobutanones from readily available alkyl- and functionalized alkyl-substituted enol ethers. The usefulness of these cyclobutanones is
Dichloroenol ethers x-ray analysis in the mechanistic elucidation of ynol ethers formation
Darses, Benjamin,Philouze, Christian,Greene, Andrew E.,Poisson, Jean-Francois
experimental part, p. 1053 - 1059 (2012/01/05)
X-ray crystallographic data are provided for dichloroenol ethers (S,E)-2-(1-(1,2-dichlorovinyloxy)ethyl)-1,3,5-triisopropylbenzene (2) and (S,E)-2-(1-(1,2-dichloroprop-1-enyloxy)ethyl)-1,3,5-triisopropylbenzene (3). The former forms colorless crystals (or
Extending the scope of the [2+2] cycloaddition of dichloroketene to chiral enol ethers: Synthesis of (-)-detoxinine
Ceccon, Julien,Poisson, Jean-Fran?ois,Greene, Andrew E.
, p. 1413 - 1416 (2007/10/03)
Allylic oxidation of a known lactam, obtained by asymmetric [2+2] cycloaddition of dichloroketene to a chiral enol ether, followed by Beckmann ring expansion and dechlorination, affords a potential intermediate for the synthesis of various natural product
New asymmetric approach to natural pyrrolizidines: Synthesis of (+)-amphorogynine A, (+)-amphorogynine D, and (+)-retronecine
Roche, Caroline,Kadlecikova, Katarina,Veyron, Amael,Delair, Philippe,Philouze, Christian,Greene, Andrew E.,Flot, David,Burghammer, Manfred
, p. 8352 - 8363 (2007/10/03)
Three natural pyrrolizidines, (+)-amphorogynines A and D and (+)-retronecine, have been prepared from a common lactam intermediate. This central compound, in turn, was synthesized in diastereomerically enriched form through a highly selective [2 + 2]-cycl
Dichloroketene-chiral olefin-based approach to pyrrolizidines: Highly stereocontrolled synthesis of (+)-amphorogynine A
Roche, Caroline,Delair, Philippe,Greene, Andrew E.
, p. 1741 - 1744 (2007/10/03)
(Matrix presented) A highly stereoselective route to (+)-amphorogynine A, a novel pyrrolizidine recently isolated from the New Caledonian plant Amphorogynine spicata, has been realized. The key step in the approach is a diastereoselective [2 + 2] dichloro
Enantiocontrolled preparation of indolizidines: Synthesis of (-)-2-epilentiginosine and (+)-lentiginosine
Rasmussen,Delair,Greene
, p. 5438 - 5443 (2007/10/03)
A highly stereoselective approach to (-)-2-epilentiginosine and (+)-lentiginosine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether. The two naturally occurring indolizidines are each obtained enantioselectively (≥ 99:1) in ca. 8.5% overall yield.
