188816-35-5Relevant academic research and scientific papers
A general strategy for the synthesis of enantiomerically pure azetidines and aziridines through nickel-catalyzed cross-coupling
Jensen, Kim L.,Nielsen, Dennis U.,Jamison, Timothy F.
, p. 7379 - 7383 (2015/05/13)
Abstract In this communication, we report a straightforward synthesis of enantiomerically pure 2-alkyl azetidines. The protocol is based on a highly regioselective nickel-catalyzed cross-coupling of aliphatic organozinc reagents with an aziridine that fea
Reactivity of activated versus nonactivated 2-(bromomethyl)aziridines with respect to sodium methoxide: A combined computational and experimental study
Goossens, Hannelore,Vervisch, Karel,Catak, Saron,Stankovic, Sonja,D'Hooghe, Matthias,De Proft, Frank,Geerlings, Paul,De Kimpe, Norbert,Waroquier, Michel,Van Speybroeck, Veronique
, p. 8698 - 8709 (2012/01/05)
The difference in reactivity between the activated 2-bromomethyl-1- tosylaziridine and the nonactivated 1-benzyl-2-(bromomethyl)aziridine with respect to sodium methoxide was analyzed by means of DFT calculations within the supermolecule approach, taking into account explicit solvent molecules. In addition, the reactivity of epibromohydrin with regard to sodium methoxide was assessed as well. The barriers for direct displacement of bromide by methoxide in methanol are comparable for all three heterocyclic species under study. However, ring opening was found to be only feasible for the epoxide and the activated aziridine, and not for the nonactivated aziridine. According to these computational analyses, the synthesis of chiral 2-substituted 1-tosylaziridines can take place with inversion (through ring opening/ring closure) or retention (through direct bromide displacement) of configuration upon treatment of the corresponding 2-(bromomethyl)aziridines with 1 equiv of a nucleophile, whereas chiral 2-substituted 1-benzylaziridines are selectively obtained with retention of configuration (via direct bromide displacement). Furthermore, the computational results showed that explicit accounting for solvent molecules is required to describe the free energy profile correctly. To verify the computational findings experimentally, chiral 1-benzyl-2-(bromomethyl)aziridines and 2-bromomethyl-1-tosylaziridines were treated with sodium methoxide in methanol. The presented work concerning the reactivity of 2-bromomethyl-1- tosylaziridine stands in contrast to the behavior of the corresponding 1-tosyl-2-(tosyloxymethyl)aziridine with respect to nucleophiles, which undergoes a clean ring-opening/ring-closure process with inversion of configuration at the asymmetric aziridine carbon atom.
L-Threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-morita-Baylis-Hillman reaction
Zhong, Fangrui,Wang, Youqing,Han, Xiaoyu,Huang, Kuo-Wei,Lu, Yixin
supporting information; experimental part, p. 1310 - 1313 (2011/04/26)
A series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. l-Threonine-derived phosphine
Solution- and solid-phase synthesis of 4-hydroxy-4,5-dihydroisoxazole serivatives from enantiomerically pure N-tosyl-2,3-aziridine alcohols
Righi, Paolo,Scardovi, Noemi,Marotta, Emanuela,Holte, Peter Ten,Zwanenburg, Binne
, p. 497 - 500 (2007/10/03)
(formula presented) Enantiomerically pure N-tosyl-2,3-aziridine alcohols are directly converted into 4-hydroxy-4,5-dihydroisoxazole 2-oxides through oxidation to the corresponding aldehydes followed by in situ tandem nitroaldol-intramolecular cyclization.
