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 journalArticle

Abstract

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
DOIs
Publication statusPublished - 1993

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    Bailey, P. D., Hollinshead, S. P., McLay, N. R., Morgan, K., Palmer, S. J., Prince, S. N., Reynolds, C. D., & Wood, S. D. (1993). Diastereo- and enantio-selectivity in the Pictet-Spengler reaction. Journal of the Chemical Society, Perkin Transactions 1, (4), 431-439. https://doi.org/10.1039/P19930000431