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Aryl and alkyl chiral oxazolidine sulfonium salts with cis and trans dispositions derived from (–)‐(R)‐2‐phenylglycinol were demonstrated to be good to excellent chiral auxiliaries for the diastereoselective synthesis of (2R,3S)‐trans‐epoxyamides. Interestingly, the diastereoselective outcome depends on the stereochemistry of the chiral center at the C‐4 position of the oxazole moiety. The stereoselectivities were consistent even for aliphatic aldehydes.

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Key indicatorsSingle-crystal X-ray study T = 296 K Mean '(C±C) = 0.006 A Ê R factor = 0.058 wR factor = 0.167 Data-to-parameter ratio = 22.2 For details of how these key indicators were automatically derived from the article, seeThe crystal structure of the title compound, C 13 H 15 NOS, is very similar to that of the corresponding oxazolopyridin-5one. However, a signi®cant participation of a tautomeric thio± enolic form is observed, as re¯ected by the short NÐC( S) bond length of 1.328 (4) A Ê .

Ethyl 2-((S)-1-phenylethylamino)acetate, 2. To a stirred solution of (S)phenylethylamine (1 g, 7.8 mmol, 1 eq) in 40 mL of CH 3 CN was added the ethyl 2bromoacetate (0.865 mL, 7.8 mmol, 1 eq) and K 2 CO 3 (2.15 g, 15.6 mmol, 2 eq).The reaction mixture was stirred for 2 h at room temperature. Finally, the mixture was filtered and the solvent was evaporated under reduced pressure. The crude