(3R,4S)-3,4-Isopropylidenedioxy-3,4-dihydro-2H-pyrrole 1-oxide

[EN] The title compound C7H11NO3 was prepared by intramolecular nucleophilic displacement of 2,3-O-iso-propylidene-D-erythronolactol. There are two molecules in the asymmetric unit, which are related by a pseudo-inversion centre. The crystal structure determination confirms unequivocally the configuration of the chiral centres as 3S,4R. In the crystal structure, intermolecular C-H center dot center dot center dot O interactions link the molecules (into infinite zigzag chains along the a axis.The authors are grateful to the MICINN (CTQ2009-11172), Junta de Castilla y Leon, for financial support (GR178 and SA001A09) and for the doctoral fellowships awarded to MFF.Flores, M.; García García, P.; Garrido, N.; Sanz, F.; Diez, D. (2011). (3R,4S)-3,4-Isopropylidenedioxy-3,4-dihydro-2H-pyrrole 1-oxide. Acta Crystallographica Section E. 67:1116-1117. https://doi.org/10.1107/S1600536811013055S1116111767Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.Cicchi, S., Corsi, M., Brandi, A., & Goti, A. (2002). Straightforward Synthesis of Enantiomerically Pure (3S,4R)- and (3R,4S)-3,4-Isopropylidenedioxypyrroline 1-Oxide, Precursors of Functionalizedcis-Dihydroxy Azaheterocycles, by a Novel «One-Pot» Procedure. The Journal of Organic Chemistry, 67(5), 1678-1681. doi:10.1021/jo0157573Cicchi, S., Marradi, M., Vogel, P., & Goti, A. (2006). One-Pot Synthesis of Cyclic Nitrones and Their Conversion to Pyrrolizidines: 7a-epi-Crotanecine Inhibits α-Mannosidases. The Journal of Organic Chemistry, 71(4), 1614-1619. doi:10.1021/jo0523518Closa, M., & Wightman, R. H. (1998). Synthesis of (3S,4R)-3,4-Isopropylidenedioxy-1-pyrroline-n-oxide, an Enantiopure Functionalized Cyclic Nitrone; Cycloaddition Reactions with Dimethyl Maleate and Dimethyl Fumarate. Synthetic Communications, 28(18), 3443-3450. doi:10.1080/00397919808004452Döpp, D. & Döpp, H. (1990). In Houben-Weyl - Methoden der Organischen Chemie, Vol. E14b, edited by D. Klamann & H. Hagemann. Stuttgart: Georg Thieme.Flack, H. D. (1983). On enantiomorph-polarity estimation. Acta Crystallographica Section A Foundations of Crystallography, 39(6), 876-881. doi:10.1107/s0108767383001762Flores, M. F., Núñez, M. G., Moro, R. F., Garrido, N. M., Marcos, I. S., Iglesias, E. F., … Díez, D. (2010). Synthesis of a New Chiral Pyrrolidine. Molecules, 15(3), 1501-1512. doi:10.3390/molecules15031501Hamer, J., & Macaluso, A. (1964). Nitrones. Chemical Reviews, 64(4), 473-495. doi:10.1021/cr60230a006Keleşoğlu, Z., Gültekin, Z., & Büyükgüngör, O. (2010). N-[(Z)-4-Methoxybenzylidene](methoxycarbonyl)methanamine oxide. Acta Crystallographica Section E Structure Reports Online, 66(9), o2332-o2333. doi:10.1107/s1600536810032289Lombardo, M., & Trombini, C. (2002). The Reaction of Nitrones with Organometallic Compounds: Scope, Limitations and Synthetic Applications. Current Organic Chemistry, 6(8), 695-713. doi:10.2174/1385272023373987Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., … van de Streek, J. (2006). Mercury: visualization and analysis of crystal structures. Journal of Applied Crystallography, 39(3), 453-457. doi:10.1107/s002188980600731xMcCaig, A. E., Meldrum, K. P., & Wightman, R. H. (1998). Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (−)-lentiginosine. Tetrahedron, 54(32), 9429-9446. doi:10.1016/s0040-4020(98)00572-9Sheldrick, G. M. (2007). A short history ofSHELX. Acta Crystallographica Section A Foundations of Crystallography, 64(1), 112-122. doi:10.1107/s0108767307043930Tufariello, J. J. (1984). In 1,3-Dipolar Cycloaddition Chemistry, edited by A. Padwa. New York: John Wiley & Sons