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Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction: A highly efficient route toCis-1,3-disubstituted tetrahydro-β-carbolines

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(00)73247-3

Abstract

Abstract Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spengler reaction between tryptophan esters and aldehydes can be controlled by varying the size of the ester group; the reaction proceeds in essentially quantitative yield with most aldehydes when conducted in chloroform in the presence of molecular sieves.

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