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Principles and Applications of Stereochemistry. By M. North
Molecules 1999, 4(7), 169-179; doi:10.3390/40700169
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Polyalkoxy Nitrones as Chiral Building Blocks in Asymmetric Synthesis

*  and
Departamento de Quimica Organica, Universidad de Zaragoza, E-50009 Zaragoza, Aragon, Spain
* Author to whom correspondence should be addressed.
Received: 23 December 1998 / Revised: 20 March 1999 / Accepted: 29 May 1999 / Published: 4 June 1999
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Abstract

Optically active nitrones derived from both aldoses and dialdoses add metallated heterocycles in a stereocontrolled way depending on the nature of the Lewis acid used as a precomplexing agent of the nitrone. Further elaborations of the resulting hydroxylamines lead to the development of new synthetic methodologies for the preparation of polyalkoxy α-amino aldehydes and α-amino acids. These compounds can be used as key advanced intermediates in the synthesis of a wide range of natural products and derivatives including amino sugars, aza sugars, and complex nucleosides.
Keywords: Nitrones; hydroxylamines; carbohydrates; aminoacids; aminoaldehydes Nitrones; hydroxylamines; carbohydrates; aminoacids; aminoaldehydes
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Merino, P.; Tejero, T. Polyalkoxy Nitrones as Chiral Building Blocks in Asymmetric Synthesis. Molecules 1999, 4, 169-179.

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