Enantiopure tetrahydro-β-carbolines via Pictet-Spengler reactions with N-sulfinyl tryptamines

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1955-1958

  Gremmen, Christiaan ^a   Willemse, Bianca ^a   Wanner, Martin J ^a   Koomen, Gerrit Jan ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000219741     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006034t     Document Type: Article

References (32)

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25. General procedure: A solution of the sulfinamide (0.2 mmol) and the aldehyde (1.0 mmol) in dry methylene chloride/chloroform (2 mL) was cooled to -78 °C. The indicated quantity of CSA was added, and the reaction mixture was stirred at -78 °C for the indicated time. The reaction was quenched with triethylamine, and the solvents were removed in vacuo. Purification using column chromatography (silica gel, 1:1 light petroleum/ ethyl acetate) yielded the mixture of diastereomers.
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28. 4 (200 mL, 0.1 M). Extractive workup and recrystallization (ethyl actetate) yielded (R)-3a (73%).
29. In principle, regeneration of the Andersen reagent is possible when the chiral auxiliary is removed in the presence of (-)-menthol.
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