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1H NMR that is now understood to indicate a 1:2 mixture of ent-44: [ent-45 + 45]. The more stable oxazaborolidine fraction (trans B-phenyl and C-phenyl) was separated by chromatography, hydrolyzed to 46 (methanol, reflux) followed by ethylenediamine, and derivatized with (S)-2-chloropropionyl chloride. This produced a ca. 4:1 mixture of (S,R):(S,S) N-(α-chloropropionyl)-α-methylphenylglycine diastereomers, identified by chemical shift comparison with the authentic isomers reported by Kellogg et al. (ref 11). The initial ratio of alkylation products ent-44:[ent-45 + 45] is consistent with the observed diastereomer ratio if ca. 20-30% of the original ent-44 had isomerized to 45.
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