Stereoselective conjugate radical additions: application of a fluorous oxazolidinone chiral auxiliary for efficient tin removal.
[reaction: see text] A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazolidinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.
Hein
Jason E
JE
Department of Chemistry, University of Manitoba, Winnipeg, MB, R3T 2N2 Canada.
Zimmerman
Jake
J
Sibi
Mukund P
MP
Hultin
Philip G
PG
D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D006845:Hydrocarbons, Fluorinated; D009947:Organotin Compounds; D023303:Oxazolidinones