Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesis of (S)-(+)-coniine.
The one-pot three-component addition reaction of trimethylsilylacetylene, aldehydes and dibenzylamine provides in the presence of CuBr/Quinap as catalyst, various enantiomerically enriched propargylamines in good yields (up to 99%) and excellent enantiomeric excess (up to 98%ee) which can be used as a key intermediate in the synthesis of the alkaloid (S)-(+)-coniine.
Gommermann
Nina
N
Department Chemie, Ludwig-Maximilians-Universität München, Germany.
Knochel
Paul
P