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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > September  >
In the Laboratory
Chemistry of Natural alpha-Amino Acids: A Surprising "One-Pot Four-Step" Conversion of Polyfunctional Enones into Cyclic Imines
Sonia Amigoni, Christophe Penverne, Caroline Nugier-Chauvin, and Yves Le FlocÕh*
Ecole Nationale Supérieure de Chimie, Campus de Beaulieu, 35700 Rennes, France
Cover
September 1999
Vol. 76 No. 9
p. 1247
Abstract
This project is aimed at introducing graduate students to multistep organic synthesis. The elaboration of the proposed retrosynthetic scheme involved the use of natural a-amino acids as starting materials. The synthesis of the target polyfunctional enones allowed students to understand the importance of protective groups. They also discovered the necessity of intermediate purification even at the price of lower yields. The use of sensitive and harmful reagents such as DIBALH, for instance, led the instructors to point out laboratory work hazards and to remind students of elementary safety instructions. Hydrogenation and hydrogenolysis of these enones afforded original analogues of natural alkaloids, the structure of which was elucidated by NMR spectroscopy and IR spectrometry.
More Information
*  Citation
 Amigoni, Sonia; Penverne, Christophe; Nugier-Chauvin, Caroline; Le FlocÕh, Yves. J. Chem. Educ. 1999 76 1247.
*  Keywords
 Organic Chemistry; Laboratory Instruction; Natural Products; Amino Acids; Organic Synthesis
*  History
 Created:
Last Updated:		 July 30, 1999
June 23, 2005
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