372511-64-3Relevant articles and documents
Spirocyclopropane isoxazolidines, octahydropyrindin-4-ones and β-lactams with biomimetic ethylene release from the electrophilic substitution of a 1,1-ethyleneallylzinc complex
Paschetta,Cordero,Paugam,Ollivier,Brandi,Salaün
, p. 1233 - 1236 (2001)
Electrophilic substitution of 1-ethenylcyclopropyl mesylate by 3,3-diethoxypropanal in the presence of palladium(0) (5%) and diethylzinc (2 equivalents) provided 5-cyclopropylidene-1,1-diethoxy-3-hydroxypentane; its nitrone derivatives underwent intramolecular cycloaddition to provide spirocyclopropane isoxazolidines, which then were transformed under thermal or acidic conditions, into octahydropyrindin-4-ones or bicyclic β-lactams with the ethylene phytohormone extrusion, respectively. Use of chiral auxiliaries, i.e, (L)-2-acetoxylactate can lead to enantiomerically enriched heterocycles.
Selective ring contraction of 5-spirocyclopropane isoxazolidines mediated by acids
Cordero, Franca M.,Pisaneschi, Federica,Salvati, Maria,Paschetta, Valentina,Ollivier, Jean,Salauen, Jacques,Brandi, Alberto
, p. 3271 - 3280 (2007/10/03)
Thermolysis of 3,4-cis ring-fused 5-spirocyclopropane isoxazolidines 16, 18-21, 33, 34, 38a, and 61, in the presence of a protic acid at 70-110 °C, yielded 3,4-cis ring-fused azetidin-2-ones 22-26, 41, 42, 46, and 62 with concomitant extrusion of ethylene
