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Condensation of tert-butyl (E)-3-(2'-aminophenyl)propenoate with a range of aromatic and heteroaromatic aldehydes gives the corresponding imines as single diastereoisomers (>98% de). Addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide initiates a tandem conjugate addition/cyclization reaction to generate 2-aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives in >98% de, >98% ee and high isolated yield. Hydrogenolysis of an N(1)-Boc protected derivative allows selective cleavage of the N-benzyl-N-alpha-methylbenzyl protecting groups without compromise of the diastereo- or enantiopurity.

Original publication

DOI

10.1021/ol9004118

Type

Journal article

Journal

Org Lett

Publication Date

07/05/2009

Volume

11

Pages

1959 - 1962

Keywords

Amides, Carboxylic Acids, Cyclization, Lithium, Molecular Structure, Organometallic Compounds, Quinolines, Stereoisomerism