Tetrahedron Asymmetry p. 1371 - 1378 (1991)
Update date:2022-08-05
Topics:
Goti, Andrea
Cicchi, Stefano
Brandi, Alberto
Pietrusiewicz, K. Michal
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.
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Doi:10.1016/j.tet.2012.06.037
(2012)Doi:10.1007/BF00957978
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(2012)