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

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.

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 Creators:
Schmidt, G1, Author
Waldmann, Herbert2, Author           
Henke, H1, Author
Burkard, M1, Author
Affiliations:
1external, ou_persistent22              
2Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753290              

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Free keywords: DIELS-ALDER REACTIONS; ESTERS; CHLORIDES Chemistry; amino acids; asymmetric syntheses; carbolines; chiral auxiliaries; Pictet-Spengler reaction;
 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.

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Language(s): eng - English
 Dates: 1996-12
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: A1996WD80600012
DOI: 10.1002/chem.19960021215
 Degree: -

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Title: CHEMISTRY-A EUROPEAN JOURNAL
Source Genre: Journal
 Creator(s):
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Publ. Info: Weinheim : WILEY-VCH
Pages: - Volume / Issue: 2 (12) Sequence Number: - Start / End Page: 1566 - 1571 Identifier: ISSN: 0947-6539