Treatment of N,N-dibenzylamino alcohols with sulfonyl chloride leads to rearranged beta-chloro amines, precursors to beta-amino acids, and not to tetrahydroisoquinolines

[GRAPHICS] Very recently, the unexpected formation of 3-substituted 1,2,3,4-tetrahydro isoquinolines starting from N,N-dibenzyl-protected beta-amino alcohols was reported, The authors claimed that treatment with tosyl chlorides induced i ntramolecular Friedel-Crafts alkylation. Reexamination of the reactions in our laboratory clearly proved rearranged chloro amines instead of the initi ally assumed tetrahydoisoquinoline structures. The chloro amines investigat ed can be employed as highly useful intermediates for an EPC synthesis of b eta-amino nitrlles and beta-amino acids.