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Communication | Regular issue | Vol 27, No. 6, 1988, pp.1357-1363
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4554
Pictet-Spengler Reactions in Aprotic Media. Stereospecific Conbersion of Optically Active cis-1,3-Disubstituted 1,2,3,4-tetrahydro-β-carbolines into Their Corresponding trans-Diastereomers

Lin-Hua Zhang and James M Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


The Pictet-Spengler reaction in refluxing benzene of D-(+)- Na,-methyl-Nb-benzyltryptophan methyl ester 1 and methyl 3-formyl-propionate 2, regioselectively, furnished the trans-1,3-disubstituted-1,2,3,4-tetrahydro-β-carboline 3 (72%) with no detectable racemization at position-3. The optically active cis-diastereomer 4 (28%), which accompanied 3, was converted (CH3OH, HCI, δ) into the trans isomer 3 via the ring-cleaved carbocation intermediate 7, followed by stereospecific intramolecular cyclization.