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

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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. (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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-72A2-6
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.