Oxazolidine Sulfur Ylides Derived from Phenylglycinol for the Specific and Highly Diastereoselective Synthesis of Aryl and Alkyl trans‐Epoxyamides

Abstract

AbstractAryl 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.