Collect. Czech. Chem. Commun. 1990, 55, 230-244

Enantioselective Diels-Alder reaction of (E)-1-trimethylsilyloxy-1,3-butadiene with chiral glyoxylates

Otakar Červinkaa, Aleš Svatošb, Petr Trškaa and Pavel Pecha

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Enantioselective Diels-Alder reaction of (E)-1-trimethylsilyloxy-1,3-butadiene (I) with chiral (-)-menthyl (II) and (-)-8-phenylmenthyl (III) glyoxylates in various solvents without or with catalysts was studied. The reactions gave a mixture of trans-and cis-isomers of (-)-menthyl (IV) and (-)-8-phenylmenthyl (V) 2-trimethylsilyloxy-5,6-dihydro-2H-pyran-6-carboxylates. The regioselectivity of the reaction was explained by quantum-chemical calculations, the enantioselectivity was determined using 13C NMR spectroscopy and the absolute configuration of the addition products was assigned on the basis of chemical correlation with (S)-(-)-dimethyl malate.