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• W2952297079 startingPage "981" @default.
• W2952297079 abstract "The first 1,3-dipolar reaction of azomethine ylides with optically pure vinyl sulfoxide are reported. The presence of the sulfinyl group increase the reactivity of the acrylate moiety as a dipolarophile, and the reactions evolve with complete regio- and endo-selectivities. Nevertheless, mixtures of the two diastereoisomers 4 and 5 (75-88% de) resulting from the anti dipole/s-cis dipolarophile and syn dipole/s-trans dipolarophile approaches, respectively, are obtained. The stereoselectivity can be controlled by using THF or MeCN as solvents or by changing the reaction temperature in MeCN. After separation of the cycloadducts, optically pure 2,5-dihydro-1H-pyrroles are easily obtained by pyrolytic desulfinylation." @default.
• W2952297079 created "2019-06-27" @default.
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• W2952297079 date "2002-01-16" @default.
• W2952297079 modified "2023-10-16" @default.
• W2952297079 title "Asymmetric 1,3-Dipolar Cycloaddition of N-Metalated Azomethine Ylides to Methyl (<i>S</i>)-2-(<i>p</i>-Tolylsulfinyl)acrylate. Synthesis of Optically Pure 2,4,5-Trisubstituted 2,5-Dihydro-1<i>H</i>-pyrroles" @default.
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• W2952297079 doi "https://doi.org/10.1021/jo010797s" @default.
• W2952297079 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11856048" @default.
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