Literature DB >> 21961580

[4 + 2] Cyclocondensation reactions of tungsten-dihydropyridine complexes and the generation of tri- and tetrasubstituted piperidines.

Daniel P Harrison1, Diana A Iovan, William H Myers, Michal Sabat, Sisi Wang, Victor E Zottig, W Dean Harman.   

Abstract

A new method for the preparation of functionalized piperidines is described in which various dihydropyridine (DHP) complexes of {TpW(NO)(PMe(3))} that are derived from pyridine-borane undergo [4 + 2] cyclocondensation with enones, enals, nitrosobenzene, and several isocyanates to form [2.2.2] bicyclic species. In several cases the diazabicyclooctene products derived from DHP complexes and isocyanates can be further elaborated into novel syn-2,5-disubstituted and 2,3,6-trisubstituted piperidinamides.

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Year:  2011        PMID： 21961580     DOI： 10.1021/ja2075086

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

1.  Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Authors:  Simon Duttwyler; Shuming Chen; Colin Lu; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-06       Impact factor: 15.336

2.  A Highly Divergent Synthesis of 3-Aminotetrahydropyridines.

Authors:  Justin H Wilde; Diane A Dickie; W Dean Harman
Journal:  J Org Chem       Date:  2020-06-04       Impact factor: 4.354

3.  Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Authors:  Rhia M Martin; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2013-01-15       Impact factor: 6.005

4.  Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.

Authors:  Michael A Ischay; Michael K Takase; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-02-11       Impact factor: 15.419

5.  Stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes.

Authors:  Li-Chao Fang; Richard P Hsung
Journal:  Org Lett       Date:  2014-03-12       Impact factor: 6.005

6.  Synthesis of spiro[indoline-3,1'-quinolizines] and spiro[indoline-3, 4'-pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles.

Authors:  Jing Sun; Hui Gong; Yan Sun; Chao-Guo Yan
Journal:  Mol Divers       Date:  2013-07-19       Impact factor: 2.943

Review 7.  Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317
  7 in total

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