TY - JOUR
T1 - Diastereoselective alkylation of 8-phenylmenthyl 2- methylacetoacetate. Preparation of enantiomerically pure 4,4-disubstituted 2-pyrazolin-5-ones
AU - Moreno-Mañas, Marcial
AU - Sebastián, Rosa M.
AU - Vallribera, Adelina
AU - Molins, Elies
AU - Espinosa, Enrique
PY - 1997/5/22
Y1 - 1997/5/22
N2 - Alkylation of (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate with alkyl halides affords 2-alkyl-2-methylacetoacetates in diastereomeric ratios 72:28 to 85:15. The major R (at C-α) diastereoisomers are converted into enantiopure 4,4-disubstituted 2-pyrazolin-5-ones with recovery of the chiral inductor.
AB - Alkylation of (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate with alkyl halides affords 2-alkyl-2-methylacetoacetates in diastereomeric ratios 72:28 to 85:15. The major R (at C-α) diastereoisomers are converted into enantiopure 4,4-disubstituted 2-pyrazolin-5-ones with recovery of the chiral inductor.
U2 - 10.1016/S0957-4166(97)00131-6
DO - 10.1016/S0957-4166(97)00131-6
M3 - Article
VL - 8
SP - 1525
EP - 1527
IS - 10
ER -