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The Journal of Organic Chemistry

Nicotinic acid lariat ethers: syntheses, complexation, and reduction

GR Newkome, CR Marston

文献索引:Newkome, George R.; Marston, Charles R. Journal of Organic Chemistry, 1985 , vol. 50, # 22 p. 4238 - 4245

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被引用次数: 28

摘要

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-l, 4-dihydropyridine 26. Lariat 26 and the nonlariat analogue 31 both reduced a, a, a-trifluoroacetophenone in ...