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  • Title: Enantioselective synthesis of 2-substituted 2-phenylethylamines by lithiation-substitution sequences: synthetic development and mechanistic pathway.
    Author: Laumer JM, Kim DD, Beak P.
    Journal: J Org Chem; 2002 Sep 20; 67(19):6797-804. PubMed ID: 12227812.
    Abstract:
    The lithiation and asymmetric substitution of N-(2-phenylethyl)isobutyramide (2) with selected electrophiles, under the influence of (-)-sparteine, provides benzylically substituted products in 58-90% yields with enantiomeric ratios (ers) from 72:28 to 91:9. Syntheses of enantioenriched dihydroisoquinolines (S)-18 and (S)-19 and a tetrahydroisoquinoline (4S)-20 provide examples of synthetic applications. Mechanistic investigations suggest the enantiodetermining step at -78 degrees C is a dynamic thermodynamic resolution.
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