The Journal of organic chemistry

Enantioselective synthesis of 2-substituted 2-phenylethylamines by lithiation-substitution sequences: Synthetic development and mechanistic pathway

JM Laumer, DD Kim, P Beak

Index: Laumer, Jason M.; Kim, Dwight D.; Beak, Peter Journal of Organic Chemistry, 2002 , vol. 67, # 19 p. 6797 - 6804

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Citation Number: 30

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 ...