Stereodivergent Diversity‐Oriented Synthesis: Exploiting the Versatility of 2‐Piperidine Ethanol

A sequence of seven reactions (stereocontrolled allylation, Mitsunobu reaction, ring closing metathesis, and amino/amido intramolecular nucleophilic addition) efficiently convert the inexpensive starting 2‐piperidine ethanol into a small library of enatiomerically pure nitrogen containing compounds...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-07, Vol.2019 (25), p.4013-4019
Main Authors: Bonandi, Elisa, Marzullo, Paola, Foschi, Francesca, Perdicchia, Dario, Presti, Leonardo Lo, Sironi, Maurizio, Pieraccini, Stefano, Gambacorta, Guido, Saupe, Joern, Dalla Via, Lisa, Passarella, Daniele
Format: Article
Language:English
Subjects:
2‐Piperidine ethanol
Allyl compounds
Chemical reactions
Diversity‐oriented synthesis
Ethanol
Metathesis
Organic chemistry
Piperidine
Piperidine alkaloids
Piperidine derivatives
Stereodivergent synthesis
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Summary:A sequence of seven reactions (stereocontrolled allylation, Mitsunobu reaction, ring closing metathesis, and amino/amido intramolecular nucleophilic addition) efficiently convert the inexpensive starting 2‐piperidine ethanol into a small library of enatiomerically pure nitrogen containing compounds characterized by three new scaffolds that present a relevant diversity. This simple approach encroaches the further exploration of the chemical space. Efficient conversion of 2‐piperidine ethanol into a small library of enantiomerically pure nitrogen containing compounds by a stereodivergent approch is described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900461