Issue 4, 2010

Catalytic asymmetric synthesis of cyclic amino acids and alkaloid derivatives: application to (+)-dihydropinidine and Selfotel synthesis

Abstract

An asymmetric synthesis of cyclic amino acids having piperidine and azepane core structures was realized starting from readily available glycine and alanine esters by combination of phase-transfer catalyzed asymmetric alkylation and subsequent reductive amination. Some of these key intermediates were successfully transformed to natural alkaloid dihydropinidine and N-methyl-D-aspartate (NMDA) antagonist Selfotel.

Graphical abstract: Catalytic asymmetric synthesis of cyclic amino acids and alkaloid derivatives: application to (+)-dihydropinidine and Selfotel synthesis

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Apr 2010
Accepted
04 Jun 2010
First published
02 Jul 2010

Chem. Sci., 2010,1, 499-501

Catalytic asymmetric synthesis of cyclic amino acids and alkaloid derivatives: application to (+)-dihydropinidine and Selfotel synthesis

T. Kano, T. Kumano, R. Sakamoto and K. Maruoka, Chem. Sci., 2010, 1, 499 DOI: 10.1039/C0SC00250J

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