(1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one

In the title compound, C₇H₁₁NO₄, prepared via a Morita–Baylis–Hillman adduct, the five-membered ring bearing three O atoms approximates to a twisted conformation, whereas the other ring is close to an envelope, with a C atom in the flap position. The dihedral angle between their mean planes (all atoms) is 23.11 (9)°. The new stereocenters are created in a trans-diaxial configuration. In the crystal, O—H...O and O—H...(O,O) hydrogen bonds link the mol­ecules, generating a three-dimensional network. A weak C—H...O inter­action also occurs.

(1S,2S,6R,7aR)-2-Benzyl-1,6-dihy­droxy­hexa­hydro­pyrrolizin-3-one

In the title compound, C₁₄H₁₇NO₃, the dihedral angles show that the H atoms at two stereocenters are in a trans-diaxial configuration. In the crystal, the molecules are linked by O—H...O hydrogen bonds. The absolute configuration of the molecule has been established on the basis of refinement of the Hooft and Flack parameters.

(1S,2E,6R,7aR)-1,6-Dihy­droxy-2-(4-nitro­benzyl­idene)-2,3,5,6,7,7a-hexa­hydro-1H-pyrrolizin-3-one

The crystal structure of the title compound, C₁₄H₁₄N₂O₅, contains two distinct conformers in the asymmetric unit. The compound has three defined stereocenters, two of them contiguous, and a C=C double bond with an E conformation. The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings. A prominent feature is a change from almost coplanar rings in one conformer to a new conformation in the second conformer, in which the mean plane of a five-membered ring is almost perpendicular to the benzene ring, with a dihedral angle 87.19 (8)°; the corresponding angle in the first conformer is 14.02 (10)°. In the crystal, molecules are linked by O—H...O and C—H...O hydrogen bonds. Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data. In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

(1S,2E,6R,7aR)-2-Benzyl­idene-1,6-dihy­droxy-2,3,5,6,7,7a-hexa­hydro-1H-pyrrolizin-3-one

In the title compound, C₁₄H₁₅NO₃, the conformation of the double bond was determined to be E, confirming the result obtained from two-dimensional NMR data. The five-membered rings of the pyrrolizine unit exhibit C-envelope conformations, with C atoms displaced from the mean planes formed by the remaining rings atoms by 0.1468 (15) and 0.5405 (17) Å. The mean planes of these rings (through all ring atoms) have a dihedral angle of 49.03 (10)°. In the crystal, mol­ecules are linked by O—H...O hydrogen bonds. The absolute configuration of the mol­ecule was established, as judged by the, as judged by the obtained values for the Hooft and Flack parameters.