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  ASYMMETRIC STEERING OF THE PICTET-SPENGLER REACTION BY MEANS OF AMINO-ACID ESTERS AS CHIRAL AUXILIARY GROUPS

Waldmann, H., SCHMIDT, G., JANSEN, M., & GEB, J. (1994). ASYMMETRIC STEERING OF THE PICTET-SPENGLER REACTION BY MEANS OF AMINO-ACID ESTERS AS CHIRAL AUXILIARY GROUPS. TETRAHEDRON, 50(41), 11865-11884. doi:10.1016/S0040-4020(01)89301-7.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-72A2-6 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-9A76-C
Genre: Journal Article

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 Creators:
Waldmann, Herbert1, Author           
SCHMIDT, G2, Author
JANSEN, M2, Author
GEB, J2, Author
Affiliations:
1Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753290              
2external, ou_persistent22              

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Free keywords: DIELS-ALDER REACTIONS; BARBIER-TYPE REACTIONS; AQUEOUS-SOLUTION; BENZYL ESTER; IMINES; STEREOSPECIFICITY; CYCLOADDITIONS; DERIVATIVES; ALKALOIDS; DIENE
 Abstract: N-beta-(3-Indolyl)ethyl amino acid esters and differently substituted aromatic aldehydes in the presence of acetic acid form iminium intermediates which at 6 degrees C to 40 degrees C undergo Pictet-Spengler cyclizations to give tetrahydro-beta-carbolines with diastereomer ratios up to 98.5:1.5. The chiral auxiliary group is removed from the heterocycles by employing a retro Strecker reaction as the key transformation.

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Language(s): eng - English
 Dates: 1994
 Publication Status: Issued
 Pages: 20
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: A1994PL15000008
DOI: 10.1016/S0040-4020(01)89301-7
 Degree: -

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Title: TETRAHEDRON
Source Genre: Journal
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Publ. Info: KIDLINGTON, OXFORD : PERGAMON-ELSEVIER SCIENCE
Pages: - Volume / Issue: 50 (41) Sequence Number: - Start / End Page: 11865 - 11884 Identifier: ISSN: 0040-4020