A Tandem Conjugate Addition/Cyclization Protocol for the Asymmetric Synthesis of 2-Aryl-4-aminotetrahydroquinoline-3-carboxylic Acid Derivatives

Stephen G. Davies, Nadeam Mujtaba, Paul M. Roberts, Andrew D. Smith, James E. Thomson

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

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-alpha-methylbenzyl protecting groups without compromise of the diastereo- or enantiopurity.

Original languageEnglish
Pages (from-to)1959-1962
Number of pages4
JournalOrganic Letters
Volume11
Issue number9
DOIs
Publication statusPublished - 7 May 2009

Keywords

  • PARALLEL KINETIC RESOLUTION
  • DIELS-ALDER REACTION
  • HOMOCHIRAL LITHIUM AMIDES
  • FORMAL TOTAL-SYNTHESIS
  • BETA-AMINO ACIDS
  • CYCLIZATION-ELIMINATION REACTION
  • MARTINELLIC ACID
  • TETRAHYDROQUINOLINE DERIVATIVES
  • FACILE SYNTHESIS
  • ALPHA,BETA-UNSATURATED ESTERS

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