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Synlett 1998; 1998(12): 1355-1356
DOI: 10.1055/s-1998-1952
DOI: 10.1055/s-1998-1952
letter
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New β-Carboline Derivatives by Double-Cyclization of Chiral α-Heteroarylmethylamino Esters
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199812/lookinside/thumbnails/10.1055-s-1998-1952-1.jpg)
Dialkylation of amino esters 2 with o-bromobromomethylheteroaromatics 1 and double-cyclization of the resulting N,N-disubstituted esters 3 via bromo-lithium exchange to tetrahydropyridine rings gives access to dicondensed 5-hydroxy-1-azabicyclo[3.3.1]nonanes 4, mostly β-carboline derivatives. The synthesis is highly stereoselective affording optically active products.
amino acid - piperidone - β-carboline - bromo-lithium exchange