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

Patrick D. Bailey, Madeleine H. Moore, Keith M. Morgan, David I. Smith, John M. Vernon

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)3587-3588
Number of pages2
JournalTetrahedron Letters
Volume35
Issue number21
DOIs
Publication statusPublished - 1994

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