Literature DB >> 16898824

Synthesis of 2,4,6-trisubstituted chiral piperidines and (-)-dendroprimine by one-pot asymmetric azaelectrocyclization protocol.

Toyoharu Kobayashi1, Futoshi Hasegawa, Katsunori Tanaka, Shigeo Katsumura.   

Abstract

[reaction: see text] Stereocontrolled synthesis of 2,4,6-trisubstituted piperidine diastereomers has been realized from common intermediates, obtained by a one-pot azaelectrocyclization protocol. Based on the method, the asymmetric synthesis of an indolizidine alkaloid, (-)-dendroprimine, was achieved.

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Year:  2006        PMID: 16898824     DOI: 10.1021/ol0614065

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.

Authors:  Franklin A Davis; He Xu; Junyi Zhang
Journal:  J Org Chem       Date:  2007-02-17       Impact factor: 4.354

2.  Redox cycloisomerization approach to 1,2-dihydropyridines.

Authors:  Barry M Trost; Berenger Biannic
Journal:  Org Lett       Date:  2015-03-11       Impact factor: 6.005

3.  A catalytic asymmetric synthesis of polysubstituted piperidines using a rhodium(I)-catalyzed [2+2+2] cycloaddition employing a cleavable tether.

Authors:  Timothy J Martin; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-19       Impact factor: 15.336

4.  A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids.

Authors:  Roland Remuson
Journal:  Beilstein J Org Chem       Date:  2007-10-02       Impact factor: 2.883

  4 in total

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