Stereodivergent methodology for the synthesis of complex pyrrolidines.
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.
Jackson
Stephen K
SK
Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, Ontario, Canada N6A 5B7.
Karadeolian
Avedis
A
Driega
Alex B
AB
Kerr
Michael A
MA
D003521:Cyclopropanes / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D008968:Molecular Conformation; D010091:Oximes / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D004952:Esters; D004987:Ethers; D010091:Oximes; D011759:Pyrrolidines