Atropoisomeric quinolinium salt promoting the access to both enantiomeric forms of methyl mandelate: a versatile NADH mimic.
Asymmetric reduction of methyl benzoylformate by a new NADH mimic is reported; depending on the hydride source used to reduce the NAD+ precursor, NADH mimics so obtained lead to an inversion of enantioselectivity, affording either (R)-methyl mandelate in 88% ee or (S)-methyl mandelate in 78% ee.
Vasse
Jean-Luc
JL
Laboratoire de Chimie Organique Fine et Hétérocyclique, I.R.C.O.F, 1, rue Tesnieres, Mont-Saint-Aignan, France 76131.
Levacher
Vincent
V
Bourguignon
Jean
J
Dupas
Georges
G
D018716:Molecular Mimicry; D009243:NAD / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*; D012492:Salts; D013237:Stereoisomerism
D011804:Quinolines; D012492:Salts; D009243:NAD