Abstract
Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)2 was found to be the most effective.
Highlights
The most common process for their been developed for the preparation of 2-oxazolines [12,13,14,15]
It was found that transforand CF53COOH (TFA) was the suitable additive for this transformation and the yield of 4a could achieve up to 91% in 1,2-dichloroethane for about half an hour (Table 1, entry 10)
2-oxzaolines 4 in a completely highly regio- and stereoselective isomerization manner. Further application of these 2-oxzaolines in catalytic asymmetric reaction is currently underway in our laboratory
Summary
2-Oxazolinesare arevery veryimportant importantfive-membered five-memberedheterocycles heterocyclesexisting existingininnumerous numerous medicinally natural products [1,2,3,4,5,6]. They widely applied synthetic intermediates, protecting, activating and directing groups in organic synthesis. The optically active 2-oxazolines are valuable chiral building blocks and ligands asymmetric catalysiscatalysis [7,8,9,10,11]. The most common process for their been developed for the preparation of 2-oxazolines [12,13,14,15].
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