Double Reductive Amination and Selective Strecker Reaction of a  D ‐Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5‐Trihydroxypiperidines | Zendy

Matassini Camilla | Zendy; Mirabella Stefania | Zendy; Goti Andrea | Zendy; Cardona Francesca | Zendy

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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.

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