A chiral solvent effect in asymmetric organocatalysis.
Proline-catalyzed aldol reactions between enolizable ketones and aromatic aldehydes can be carried out in propylene carbonate. When enantiomerically pure propylene carbonate is used, the combination of (R)-proline and (R)-propylene carbonate constitutes a matched pair, while (S)-proline and (R)-propylene carbonate constitutes a mismatched pair.
North
Michael
M
School of Chemistry and University Research Centre in Catalysis and Intensified Processing, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. michael.north@ncl.ac.uk
Villuendas
Pedro
P
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D012997:Solvents; C045990:propylene carbonate; D011392:Proline; D011407:Propane