Facile synthesis of 1,2,3,4-tetrahydro-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization

Organic Letters

Volumn 11, Issue 9, 2009, Pages 1979-1982

  Ohta, Yusuke ^a   Oishi, Shinya ^a   Fujii, Nobutaka ^a   Ohno, Hiroaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOLINE DERIVATIVE; COPPER; INDOLE DERIVATIVE; TRYPTOLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CARBOLINES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 65549162701     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900460m     Document Type: Article

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56. Other acids were less effective. For example, after indole formation with 1g, 2d, and 3d was completed, the reaction mixture was treated with polyphosphoric acid (PPA) to give 7c in only 19% yield.
57. The product 7e was obtained in 95% ee [Chiralcel OD-H, with a linear gradient of i-PrOH (20-40% over 45 min) in hexane in the presence of 0.1% Et2NH]. HPLC charts (7e and an enantiomeric mixture 7e/ent-7e) were given in the Suppoting Information.
58. It should be noted that the indole formation of Mannich adducts derived from 1g did not proceed when using aldehydes other than paraformaldehyde and amino esters.