Reaction with TosMIC and potassium tertbutoxide gave a low yield of pyrrole 8a. Construction of a saturated pyrrolidine ring could be achieved by [3+2] cycloaddition of an in situ generated azomethine ylide. Adducts 9a and 9c were isolated as single diastereoisomers, while the PMP-derivatives 9b were formed as separable diastereomers (ca. 2:1 ratio). Although minor diastereomers of 9a/c were neither isolated nor unambiguously observed in the complex crude 1 H NMR spectra, we cannot rule out their presence in the crude reaction mixtures. The stereochemistry of the major isomers was determined by NMR analysis (NOE and analysis of coupling constants) of the derived alcohols (Supporting Information). Cyclopropanation of the enone was performed under Corey-Chaykovsky conditions, giving adducts 10a/b in good yield as single diastereoisomers following chromatography (small amounts of an apparent minor diastereomer were visible in the 1 H NMR of the crude). The relative configuration of 10a was unambiguously assigned by Xray crystallography, supporting the preferential attack on the enone syn-to the diamine function, an outcome also consistent with that assigned in the azomethine cycloadditions above.