Vanadium: The Versatile Metal. ACS Symposium Series 974. Edited by Kenneth Kustin (Brandeis University), João Costa Pessoa (IST-Technical University of Lisboa), and Debbie C. Crans (Colorado St
The intramolecular reaction of oxime ethers and cyclopropane diesters results in the diastereoselective formation of substituted pyrrolo-isoxazolidines which serve as precursors to the ubiquitouspyrrolidine motif. A simple reversal of addition order of catalyst and substrate results in formation of twodiscrete diastereomers in a highly selective and predictable manner. The adducts are prepared in excellentyields from either enantiomer of an alkoxyamino-tethered cyclopropanediester, allowing efficient access tohighly substituted homochiral pyrrolidines.