Formation of a novel ring system : An unexpected intermolecular cyclization
A novel chiral ten membered heterocyclic ring is synthesised in two steps from phthalimide derivatives of (R) and (S) -2-amino-1-butanol. The structures have been unambiguously established by single crystal X-ray diffraction of one of the compounds.
Ester Formation via Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Chloroformates
The synthesis of alkyl esters from readily available alkyl halides and chloroformates was achieved for the first time using a mild Ni-catalyzed reductive coupling protocol. Unactivated primary and secondary alkyl iodides as well as glycosyl, benzyl, and aminomethyl halides were successfully employed to yield products in moderate to excellent yields with high functional group tolerance.
Zheng, Min,Xue, Weichao,Xue, Teng,Gong, Hegui
supporting information
p. 6152 - 6155
(2016/12/09)
Synthesis of phenyl and substituted phenyl 3-ethyl-2,3,5,9b-tetrahydro[1,3]oxazolo[2,3-a]isoindol-5-ones
Addition of various aryl magnesium bromides to (R) or (S)-2-(1-hydroxybutyl)phthalimide results in the formation of substituted (R) or (S)-3-hydroxy-2(1-hydroxybutyl)isoindol-1-ones which are subsequently cyclised under highly acidic conditions to give the title compounds in moderate yields.
Naira, Dinesh S.,Pauranik, Vedavati,Shaha, Amrish C.
p. 772 - 774
(2007/10/03)
Diastereoselective access to chiral non-racemic [1,3]oxazolo-[2,3-a] isoindol-5-one ring systems via o-cationic cyclization
The title compounds 4 have been prepared from suitable β-amino-alcohol 2 and phthalic anhydride (5) in a three-step sequence in moderate to good yields (58-94%). The key step of this methodology is based on an intramolecular O-cationic cyclization involving N-acyliminium species. The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.
Sikoraiova, Jana,Chihab-Eddine, Abderrahim,Marchalin, Stefan,Daich, Adam
p. 383 - 390
(2007/10/03)
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