1028192-22-4Relevant academic research and scientific papers
Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations
Delbrassinne, Arnaud,Richald, Maximilien,Janssens, Julien,Robiette, Rapha?l
supporting information, p. 2862 - 2868 (2021/06/11)
Vinylcyclopropanes are versatile intermediates in organic synthesis which undergo various rearrangements. We report a new rearrangement of vinylcyclopropane into skipped diene. A detailed mechanistic study revealed that this transformation involves regioselective ring-opening of the cyclopropane ring followed by 1,2-migration of one of the cyclopropane substituents. Interestingly, our investigations showed that skipped diene is the kinetic product of the process but formation of a more stable cyclopentene is also accessible. The fundamental understanding of the processes involved enabled the development of divergent methodologies allowing to obtain cyclopentene or skipped diene from vinylcyclopropane in a selective and controlled manner.
Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines
Mehedi, Md Shafaat Al,Tepe, Jetze J.
supporting information, p. 7219 - 7226 (2019/06/14)
This work describes an extended version of the Corey-Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of acyl imines. The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF3·OEt2. Following the same one-pot procedure, amidine imides react with the sulfur ylides to provide imidazolines.
Asymmetric sulfur-ylide-mediated formal [4+1]-annulation reaction: Scope and mechanism
Clergue, Sébastien,Rousseau, Olivier,Delaunay, Thierry,Dequirez, Geoffroy,Tran, Trieu-Van,Aakchioui, Soumia El,Barozzino-Consiglio, Gabriella,Robiette, Rapha?l
supporting information, p. 11417 - 11425 (2018/10/21)
A formal [4+1]-annulation strategy between sulfur ylides and 1,3-dienes was developed to afford functionalized cyclopentanoids. The process consists of a stereoselective cyclopropanation reaction followed, in situ, by a stereospecific MgI2-cata
Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes
Rousseau, Olivier,Delaunay, Thierry,Dequirez, Geoffroy,Trieu-Van, Tran,Robeyns, Koen,Robiette, Rapha?l
supporting information, p. 12899 - 12902 (2015/09/07)
A highly enantioselective synthesis of functionalized cyclopentanoids by a formal asymmetric (4+1) annulation strategy was developed. The methodology consists of a stereoselective cyclopropanation reaction between chiral sulfur ylides and 1,3-dienes follo
