Asymmetric reduction of α, β-unsaturated iminium salts with 1, 4-dihydronicotinamide sugar pyranosides

…, T Makino, J Oda, Y Inouye

Index: Baba, Naomichi; Makino, Taketoshi; Oda, Jun'ichi; Inouye, Yuzo Canadian Journal of Chemistry, 1980 , vol. 58, p. 387 - 392

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Citation Number: 17

Abstract

3, 3, 5-Trimethyl-2-cyclohexylidene iminium salts were reduced with 1, 4- dihydronicotinamide sugar pyranosides to give optically active 3, 3, 5- trimethylcyclohexanone in enantiomeric excess ranging over 3-31%. The product stereochemistry changed sensitively with structural variation (including anomers, epimers, and deacetylation) of sugar residues. The reduction by more simplified chiral models, N 1- ...