ASYMMETRIC PICTET-SPENGLER REACTIONS EMPLOYING AMINO-ACID ESTERS AS MEDIATORS 
OF SELECTIVITY

Waldmann, Herbert; SCHMIDT, G; JANSEN, M; GEB, J

doi:10.1016/S0040-4039(00)73800-7

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ASYMMETRIC PICTET-SPENGLER REACTIONS EMPLOYING AMINO-ACID ESTERS AS MEDIATORS OF SELECTIVITY

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

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Citation

Waldmann, H., SCHMIDT, G., JANSEN, M., & GEB, J. (1993). ASYMMETRIC PICTET-SPENGLER REACTIONS EMPLOYING AMINO-ACID ESTERS AS MEDIATORS OF SELECTIVITY. TETRAHEDRON LETTERS, 34(37), 5867-5870. doi:10.1016/S0040-4039(00)73800-7.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-9C13-9

Abstract

The Pictet-Spengler cyclization of iminium salts generated in situ from N-(beta-3-indolyl)ethyl substituted amino acid esters and differently substituted aldehydes proceeds with high stereoselectivity to deliver chiral tetrahydro-beta-carbolines with diastereomer ratios up to 98.5:1.5.