Enantioselective synthesis of 2-substituted 2-phenylethylamines by lithiation-substitution sequences: synthetic development and mechanistic pathway |
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Authors: | Laumer Jason M Kim Dwight D Beak Peter |
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Institution: | Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA. |
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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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