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Issue 5, 1991
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Chiral organometallic NADH mimics: preparation and X-ray crystal structure of racemic (RS)-[Fe(η5-C5H5)(CO)(PPh3)(1-methyl-1,4-dihydronicotinoyl)] and homochiral (R)-(–)-[Fe(η5-C5H5)(CO){PPh2(O-[(–)-menthyl])}(1-methyl-1,4-dihydronicotinoyl)] and asymmetric reduction of ethyl benzoylformate

Abstract

The racemic complex (RS)-[Fe(η5-C5H5)(CO)(PPh3)(1-methyl-1,4-dihydronicotinoyl)] has been prepared and shown to function as a NADH mimic. An X-ray crystal structure revealed that one face of the 1,4-dihydronicotinoyl moiety is essentially blocked by the triphenylphosphine ligand. The homochiral complex (R)-(–)-[Fe(η5-C5H5)(CO)(PPh2(O-[(–)-menthyl])](1-methyl-1,4-dihydronicotinoyl)] possessing the sterically demanding chiral auxiliary [Fe(η5-C5H5)(CO){PPh2(O)-(–)menthyl)}] at C-3 has also been prepared and shown to reduce ethyl benzoylformate to ethyl mandelate in 52% enantiomeric excess by a combination of steric and chelation control.

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Article type: Paper
DOI: 10.1039/P19910001027
Citation: J. Chem. Soc., Perkin Trans. 1, 1991,0, 1027-1034
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    Chiral organometallic NADH mimics: preparation and X-ray crystal structure of racemic (RS)-[Fe(η5-C5H5)(CO)(PPh3)(1-methyl-1,4-dihydronicotinoyl)] and homochiral (R)-(–)-[Fe(η5-C5H5)(CO){PPh2(O-[(–)-menthyl])}(1-methyl-1,4-dihydronicotinoyl)] and asymmetric reduction of ethyl benzoylformate

    S. G. Davies, A. J. Edwards, R. T. Skerlj, K. H. Sutton and M. Whittaker, J. Chem. Soc., Perkin Trans. 1, 1991, 0, 1027
    DOI: 10.1039/P19910001027

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