Preparative Organic Chemistry
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ChemInform Abstract: Synthesis of Enantiomerically Pure α-Substituted Propargylic Amines by Reaction of Organoaluminum Reagents with Oxazolidines.
First published: 30 May 2010
Abstract
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ChemInform Abstract
Oxazolidines (IV) prepared from (R)-phenylglycinol (I) react at 0 °C with in situ generated dialkynylalane—triethylamine complexes in the presence of Me3Al to give protected amines (VI) in high yields and diastereoselectivity. The ferrocenylmethyl group is easily removed under acidic conditions and oxidative cleavage of the chiral appendage affords the enantiopure title amines.
