192209-51-1Relevant articles and documents
Asymmetric 1,3-dipolar cycloaddition of optically active trifluoromethylated α,β-unsaturated aryl sulfones with nitrones: The use of 0-dialkylaminoethyl chiral auxiliaries
Tsuge, Hiroyasu,Okano, Takashi,Eguchi, Shoji,Kimoto, Hiroshi
, p. 1581 - 1586 (2007/10/03)
Optically active trifluoromethylated α,β-unsaturated aryl sulfones 8a-c, which have a chiral N,N-dialkylaminoethyl group on the ortho position, were synthesized from (S)-1-phenylethylamine 2 and ethyl trifluoroacetate. Asymmetric 1,3-dipolar cycloaddition of sulfones 8a-c with some selected nitrones 9a-c gave the corresponding isoxazolidines 10a-c, 11a-c and 12-15 regio- (> 98%) and diastereo-selectively (36-56% de) in 58-80% yields. The absolute configurations of the cycloadducts were assigned on the basis of X-ray crystallographic analysis of the adduct 10a and by the 1H NMR spectra. The obtained facial selectivity was rationalized by comparison of four possible stable conformers of compound 8a based on AM1 calculations.