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 90% enantiomeric exces

Nitrone cycloaddition to 2,3-dihydro-1-phenyl-1h-phosphole 1-oxide. Double asymmetric induction and kinetic resolution by a chiral nitrone / A. GOTI; S. CICCHI; A. BRANDI; K.M. PIETRUSIEWICZ. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 2:(1991), pp. 1371-1378. [10.1016/S0957-4166(00)80033-6]

Nitrone cycloaddition 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;
1991

Abstract

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 90% enantiomeric exces
1991
2
1371
1378
A. GOTI; S. CICCHI; A. BRANDI; K.M. PIETRUSIEWICZ
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/7316
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