期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 356, 期 5, 页码 1029-1037出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300888
关键词
A(3) coupling; amino acids; enzymatic resolution; multicomponent reactions; propargylic amines
资金
- FWO [Fund for Scientific Research-Flanders (Belgium)]
- University of Leuven (KU Leuven)
- University of Leuven
- Erasmus Mundus consortium
Mono- as well as dipropargylic amines were synthesized using -amino esters as inexpensive building blocks under a single catalytic system (copper bromide, 100 degrees C, 4h, toluene) where the reactant ratio (1a/2a/3a) acted as product specific switch. Both secondary (mono) as well as tertiary (di) propargylic amines formed via three- and five-component coupling exhibited wide substrate scope with moderate to good yields and satisfactory diastereoselectivity in a few cases. The practical utility of the method is enhanced by providing a facile access to enantiopure propargylic amines via lipase-catalyzed resolution along with synthesis of unsymmetrical dipropargylic amines, secondary propargylic amines bearing quaternary carbon centers and imidazolidin-2-ones.
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