J. Irurre et al., DIELS-ALDER ASYMMETRICAL SYNTHESIS IN THE PRESENCE OF THE CHIRAL TITANIUM CATALYST - APPLICATION OF THE EXPERIMENTAL-DESIGN METHODOLOGY, Afinidad, 50(448), 1993, pp. 361-365
The asymmetric Diels-Alder reaction between 3-crotonoyl-1,3-oxazolidin
one and cyclopentadiene catalyzed by the chiral titanium (IV) derivate
d from the diol (2R,3R)-bis pha'-alpha'-tetraphenyl-1,4-dioxaspiro[4.5
]de-cane is studied. Therefore, the 2f-1 Fractional Factorial Experime
ntal Design is applied, analyzing the influence of four experimental f
actors on the yield and enantioselectivity of the reaction. In the exp
erience which affords the best enantioselectivity under the experiment
al conditions studied, an e.e. = 92% with a yield of 84% in cycloadduc
ts is reached.