A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio and diastereoselective Strecker reaction.
Double Reductive Amination and Selective Strecker Reaction of a D-Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5-Trihydroxypiperidines / C. Matassini; S. Mirabella; A. Goti; F. Cardona. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2012:(2012), pp. 3920-3924. [10.1002/ejoc.201200587]
Double Reductive Amination and Selective Strecker Reaction of a D-Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5-Trihydroxypiperidines
MATASSINI, CAMILLA;MIRABELLA, STEFANIA;GOTI, ANDREA;CARDONA, FRANCESCA
2012
Abstract
A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio and diastereoselective Strecker reaction.
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