Asymmetric control in the Pictet-Spengler reaction by means of N-protected 
amino acids as chiral auxiliary groups

Schmidt, G; Waldmann, Herbert; Henke, H; Burkard, M

doi:10.1002/chem.19960021215

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Asymmetric control in the Pictet-Spengler reaction by means of N-protected amino acids as chiral auxiliary groups

MPS-Authors

/persons/resource/persons98735

Waldmann, Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Schmidt, G., Waldmann, H., Henke, H., & Burkard, M. (1996). Asymmetric control in the Pictet-Spengler reaction by means of N-protected amino acids as chiral auxiliary groups. CHEMISTRY-A EUROPEAN JOURNAL, 2(12), 1566-1571. doi:10.1002/chem.19960021215.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-71F1-D

Abstract

Aromatic and aliphatic Schiff bases of tryptamine react with Fmoc- or ph-thaloyl-protected amino acid chlorides to form N-acyliminium intermediates, which, in the presence of titanium alkoxides at room temperature, undergo Pictet-Spengler reactions to give tetrahydro-beta-carbolines with diastereomeric ratios of up to 99:1. The chiral auxiliary can be removed from the Pictet-Spengler adducts by means of a simple reduction. To rationalize the observed stereoselectivity a transition-state model is proposed in which the titanium atom coordinates both the carbonyl group of the N-acyliminium ion and the amino acid protecting group.