Tetrahedron: Asymmetry

Stereoselective reductions with macrocyclic NADH models

U Gran, O Wennerström, G Westman

Index: Gran, Ulrik; Wennerstroem, Olof; Westman, Gunnar Tetrahedron Asymmetry, 2000 , vol. 11, # 14 p. 3027 - 3040

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Citation Number: 22

Abstract

Macrocyclic NADH models with two (C2 symmetry) or four (D2 symmetry) nicotinamide units comprised in a ring have been prepared and found to reduce activated carbonyl compounds in good yields and high enantiomeric excess. The roles of magnesium ions as a cocatalyst and the temperature have also been investigated. The smaller, C2-symmetric macrocycle gave 96% ee upon reduction of ethyl benzoylformate whereas the best result with the ...

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