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Enantiomerically pure Indoloquinolizines from tryptophane
Author(s) -
Peng Shiqi,
Winterfeldt Ekkehard
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900159
Subject(s) - chemistry , potassium carbonate , diastereomer , methyl vinyl ketone , enantiomer , ketone , catalysis , potassium , pictet–spengler reaction , organic chemistry , methyl ketone
Carboline derivatives 8 and 11 , obtained from L‐tryptophane methyl ester in a Pictet‐Spengler reaction with the corresponding acetals 6 and 10 , add methyl vinyl ketone to form the diastereomeric mixtures 9 and 12 . Under phase‐transfer conditions only 12 can be converted into a mixture of the title compounds 2a and 2b . With potassium carbonate as catalyst, however, 2b can be converted into 2c , the enantiomer of 2a .
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