Stereodivergent Methodology for the Synthesis of Complex Pyrrolidines
- 28 February 2008
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (12), 4196-4201
- https://doi.org/10.1021/ja710289k
Abstract
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.This publication has 20 references indexed in Scilit:
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