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2005
Alkaloids
U 0600
13- 220
Practically Highly Enantioselective Synthesis of Terminal Propargylamines.
An Expeditious Synthesis of (S)-(+)-Coniine. — The one-pot three-component addition reaction of aldehydes (I), trimethylsilylacetylene (II) and dibenzylamine (III) in
the presence of CuBr/Quinap as catalyst provides various enantiomerically enriched
propargylamines (IV) in high yields and enantioselectivities. Compounds (IV) can
further be functionalized by alkylation or cross-coupling reactions. Such modification
is used for short synthesis of the alkaloid (S)-coniine (VIII). — (GOMMERMANN,
N.; KNOCHEL*, P.; Chem. Commun. (Cambridge) 2004, 20, 2324-2325;
Fachbereich Chem., Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany;
Eng.) — M. Paetzel
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