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

Autor:	Colin D. Reynolds, Sarah J. Palmer, Sean P. Hollinshead, Stephen N. Prince, S. D. Wood, Neil R. McLay, Keith M. Morgan, Patrick D. Bailey
Rok vydání:	1993
Předmět:	Benzaldehyde chemistry.chemical_compound Pictet–Spengler reaction chemistry Enantio selectivity Stereochemistry Crystallographic data Molecule Crystal structure Kinetic control Nmr data
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :431-439
ISSN:	1364-5463 0300-922X
Popis:	The factors that control the relative and absolute stereochemistry of 1,3-disubstituted and 1,2,3-trisubstituted tetrahydro-β-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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::608a2585ddee3fa1e4a1cde3b65b1c5a https://doi.org/10.1039/p19930000431 Zobrazit plný text záznamu