10575-07-2Relevant academic research and scientific papers
Cornforth–Evans Transition States in Stereocontrolled Allylborations of Epoxy Aldehydes
Freund, Robert R. A.,van den Borg, Matthias,Gaissmaier, Daniel,Schlosser, Robin,Jacob, Timo,Arndt, Hans-Dieter
, p. 8639 - 8650 (2020)
Allylboration reactions rank among the most reliable tools in organic synthesis. Herein, we report a general synthesis of trifunctionalized allylboronates and systematic investigations of their stereocontrolled transformations with substituted aldehyde substrates, in order to efficiently access diverse, highly substituted target substrates. A peculiar transition in stereocontrol was observed from the polar Felkin–Anh (PFA) to the Cornforth–Evans (CE) model for alkoxy- and epoxy-substituted aldehydes. CE-type transition states were uniformly identified as minima in advanced, DFT-based computational studies of allylboration reactions of epoxy aldehydes, conforming well to the experimental data, and highlighting the underestimated relevance of this model. Furthermore, a mechanism-based rationale for the substitution pattern of the epoxide was delineated that ensures high levels of stereocontrol and renders α,β-epoxy aldehydes generally applicable substrates for target synthesis.
Methods for the preparation of allenes employing indium- and zinc-mediated dehalogenation reactions in aqueous solutions
Lin, Mei-Huey,Tsai, Wen-Shing,Lin, Long-Zhi,Hung, Shiang-Fu,Chuang, Tsung-Hsun,Su, Yi-Jen
, p. 8518 - 8523 (2012/01/19)
Simple and mild methods for the synthesis of allenes, employing indium- and zinc-mediated dehalogenation reactions of vicinal dihalides in an aqueous solvent, are described. By using these procedures, various allenylmethyl aryl ethers and monosubstituted
Chemistry of gem-Dihalocyclopropanes. XVIII. Reactions of gem-Dibromocyclopropylmethyl Sulfides with Methyllithium
Arct, Jacek,Skattebol, Lars
, p. 593 - 598 (2007/10/02)
gem-Dibromocyclopropyl sulfides 3 were prepared in good yields from 1,1-dibromo-2-iodomethylcyclopropane 4 and the appropriate sodium thiolate.Compounds 3 reacted with methyllithium to give products that were separated into low and high boiling fractions.
