Chiral organometallic NADH mimics: Highly stereoselective reductions of ethyl benzoylformate with a 1,4-dihydronicotinoyl fragment attached to the homochiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] and possessing a homochiral β-hydroxy-carboxamide at C-5.

Add time:08/03/2019    Source:sciencedirect.com

A series of homochiral organometallic NADH mimics incorporating the chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] at the C-3 carbonyl and a chiral carboxamide at C-5 of a 1,4-dihydronicotinoyl fragment have been prepared. These complexes were shown to stereoselectively reduce ethyl benzoylformate to either (R)- or (S)-ethyl mandelate by a combination of steric and chelation control. For example, complex (R,R)-12 bearing a carboxamide derived from (R)-(+)-methylbenzylamine afforded (R)-ethyl mandelate in 89% enantiomeric excess. Utilisation of complexes (R,S)-19a and (R,R,S)-22a bearing chiral β-hydroxy-carboxamides derived from valinol and norephedrine respectively gave the (R)-ethyl mandelate in greater than 97% enantiomeric excess.

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