931-12-4Relevant academic research and scientific papers
Strong hyperconjugative interactions limit solvent and substituent influence on conformational equilibrium: The case of cis-2-halocyclohexylamines
Francisco, Camila B.,Fernandes, Cleverton S.,de Melo, Ulisses Z.,Rittner, Roberto,Gauze, Gisele F.,Basso, Ernani A.
, p. 818 - 829 (2019)
The presence of strong stereoelectronic interactions involving the substituents in cis-2-substituted cyclohexanes may lead to results different from those expected. In this work, we studied the conformational behavior of cis-2-fluoro- (F), cis-2-chloro- (
Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes
Legnani, Luca,Prina-Cerai, Gabriele,Delcaillau, Tristan,Willems, Suzanne,Morandi, Bill
, p. 434 - 439 (2018/11/21)
Primary amines are essential constituents of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains challenging. Here, we report a general strategy to access primary amines from alkenes through an operationally simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative and benign sodium chloride act as the respective nitrogen and chlorine sources. The reaction proceeds at room temperature under air; tolerates a large scope of aliphatic and conjugated alkenes, including densely functionalized substrates; and provides excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity of the 2-chloroalkylamine products, an understudied class of amphoteric molecules, enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido amines, and homoallylic amines.
Catalytic asymmetric ring openings of Meso and terminal aziridines with halides mediated by chiral 1,2,3-triazolium silicates
Ohmatsu, Kohsuke,Hamajima, Yuta,Ooi, Takashi
supporting information; experimental part, p. 8794 - 8797 (2012/07/02)
Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent
