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Double Reductive Amination and Selective Strecker Reaction of a D ‐Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5‐Trihydroxypiperidines
Author(s) -
Matassini Camilla,
Mirabella Stefania,
Goti Andrea,
Cardona Francesca
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200587
Subject(s) - reductive amination , chemistry , strecker amino acid synthesis , aldehyde , amination , stereochemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis
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.