475110-77-1Relevant academic research and scientific papers
Stereodivergent methodology for the synthesis of complex pyrrolidines
Jackson, Stephen K.,Karadeolian, Avedis,Driega, Alex B.,Kerr, Michael A.
, p. 4196 - 4201 (2008/12/20)
The intramolecular reaction of oxime ethers and cyclopropane diesters results in the diastereoselective formation of substituted pyrrolo- isoxazolidines which serve as precursors to the ubiquitous pyrrolidine motif. A simple reversal of addition order of catalyst and substrate results in formation of two discrete diastereomers in a highly selective and predictable manner. The adducts are prepared in excellent yields from either enantiomer of an alkoxyamino-tethered cyclopropanediester, allowing efficient access to highly substituted homochiral pyrrolidines.
