Diastereo- and enantio-selectivity in the Pictet-Spengler reaction

Patrick D. Bailey, Sean P. Hollinshead, Neil R. McLay, Keith Morgan, Sarah J. Palmer, Stephen N. Prince, Colin D. Reynolds, Stephen D. Wood

Research output: Contribution to journalArticlepeer-review

109 Citations (Scopus)


The factors that control the relative and absolute stereochemistry of 1,3-disubstituted and 1,2,3-trisubstituted tetrahydro-ß-carbolines formed via the Pictet-Spengler reaction are discussed. In particular, the stereochemical factors that lead to the predominance of cis-1,3-disubstituted products under conditions of kinetic control are presented, with the aid of X-ray crystallographic data on a number of compounds; methods for assigning relative stereochemistry on the basis of NMR data are given; the mechanism by which racemisation can occur during the Pictet-Spengler reaction has also been studied, and procedures for eliminating this problem are given.

Original languageEnglish
Pages (from-to)431-439
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
Publication statusPublished - 1993


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