Stereoselectivity during a Dieckmann Analogous Cyclization of (Piperazin-2-yl)propionic Acid Esters-Reference-Cited by-同舟云学术

Stereoselectivity during a Dieckmann Analogous Cyclization of (Piperazin-2-yl)propionic Acid Esters

Published:2005-10-01 Issue:10 Volume:60 Page:1068-1070
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:
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Author:

Geiger Christian¹,Zelenka Christel¹,Fröhlich Roland²,Wibbeling Birgit²,Wünsch Bernhard¹

Affiliation:

1. 1Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhelms-Universität Münster, Hittorfstraße 58-62, D-48149 Münster, Germany

2. 2Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstr. 40, D-48149 Münster, Germany

Abstract

The primary Dieckmann cyclization product of the methyl (3,6-dioxopiperazin-2-yl)propionate was trapped with chlorotrimethylsilane and recrystallized. The X-ray crystal structure analysis showed (S)-configuration of the novel chiral centre. This configuration supports the hypothesis that formation of the stable lithium chelate is responsible for shifting this unusual Dieckmann cyclization towards the bicyclic product.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2005-1008/pdf

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