Nicotinic Acid Lariat Ethers: Syntheses, Complexation, and Reduction

Article abstract of DOI:10.1021/jo00222a011

Combination of 2-(hydroxymethyl)-5-oxazolinylpyridine 16a with lariat ethers 21 and 23 generated chiral 6-methylnicotinic oxazoline lariat ethers 22 and 24, respectively.Chiral lariat ether 24b by stereoselective metal-directed addition of methylmagnesium bromide was converted to the corresponding enantiomerically enriched N-magnesio-1,4-dihydropyridine 26.Lariat 26 and the nonlariat analogue 31 both reduced α,α,α-trifluoroacetophenone in a NADH model-like reduction to give the S alcohol 32 in low enantiomeric excess.