Literature DB >> 15987188

Development of a stepwise [3 + 3] annelation to functionalized piperidines.

Katharine M Goodenough1, Piotr Raubo, Joseph P A Harrity.   

Abstract

[reaction: see text] A stepwise formal [3 + 3] cycloaddition sequence via a Grignard addition-cyclization reaction leads to a much improved piperidine synthesis. This methodology provides improved flexibility in both the aziridine substrate and TMM equivalent.

Entities:  

Year:  2005        PMID： 15987188     DOI： 10.1021/ol050965t

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


  7 in total

1.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

2.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

3.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

4.  Total synthesis of (+)-lepadin F.

Authors:  Gang Li; Richard P Hsung; Brian W Slafer; Irina K Sagamanova
Journal:  Org Lett       Date:  2008-09-27       Impact factor: 6.005

5.  A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.

Authors:  Yu Zhang; Aleksey I Gerasyuto; Quincy A Long; Richard P Hsung
Journal:  Synlett       Date:  2008-01-01       Impact factor: 2.454

6.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

7.  Pd-catalysed [3 + 3] annelations in the stereoselective synthesis of indolizidines.

Authors:  Olivier Y Provoost; Andrew J Hazelwood; Joseph P A Harrity
Journal:  Beilstein J Org Chem       Date:  2007-02-08       Impact factor: 2.883
  7 in total

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