139254-73-2Relevant academic research and scientific papers
Synthesis and X-ray study of Hexahydro- and tetrahydrophospholo-[2,3-d]isoxazoles, a new class of heterocycles of potential fungicidal activity
Machetti, Fabrizio,Anichini, Beatrice,Cicchi, Stefano,Brandi, Alberto,Wieczorek, Wanda,Pietrusiewicz, K. Michal,Gehret, Jean-Claude
, p. 1091 - 1098 (1996)
Hexahydro-, 5b-I and 6a,f,I and tetrahydrophospholo[2,3-d]isoxazoles 8, 9 and 10 were synthesized by 1,3-dipolar cycloaddition of nitrones 3b-I and benzonitrile oxide (4) to 2,3-dihydro-1-phenyl-1H-phosphole 1-oxide (1) and 2,3-dihydro-1-ethoxy-1H-phosphole 1-oxide (2). The structural assignment to the compounds was confirmed by an X-ray study of two compounds of the series Sa and 5m. The compounds show a good activity as fungicides against Plasmopara viticola on vines and against Botrytis cinerea on apples. Compounds 5a-d showed weak to moderate activity as herbicides.
Nitrone Cycloadditions to 2,3-Dihydro-1-phenyl-1H-phosphole 1-Oxide. Double Asymmetric Induction and Kinetic Resolution by a Chiral Nitrone
Goti, Andrea,Cicchi, Stefano,Brandi, Alberto,Pietrusiewicz, K. Michal
, p. 1371 - 1378 (2007/10/02)
The cycloadditions of nitrones with 2,3-dihydro-1-phenyl-1H-phosphole 1-oxide give a single cycloadduct deriving from a highly diastereoselective approach of the nitrone anti to the phenyl ring of phospholene oxide.When the chiral gliceraldehyde derived nitrone is used, only two diastereoisomers are produced in 1.7:1 ratio.The structural assignment based on NMR data and X-ray analysis of the major isomer established a trans C3-C4 stereochemistry (derived from endo TS with respect to nitrone) and a C3-C4' relative stereochemistry of threo type in the major isomer and erythro in the minor one.Therefore, each enantiomer of phospholene oxide 6 gives exclusively one cycloadduct with five contiguous stereogenic centres in an established and predictable absolute configuration.The difference of reactivity of the two enantiomers allowed a partial kinetic resolution of the racemic phospholene oxide, affording (+)-(S) enantiomer with 90percent enantiomeric excess.
