Literature DB >> 10964386

The first regioselective alpha-deprotonation and functionalization of allenamides. An application in intramolecular Pauson-Khand-type cycloadditions.

H Xiong1, R P Hsung, L L Wei, C R Berry, J A Mulder, B Stockwell.   

Abstract

[rection: see text] The first regioselective alpha-deprotonation and functionalization of electron-deficient allenamines are described here. The acidities of alpha- and gamma-allenic protons of these allenamides are readily differentiated using strong bases, thereby allowing regioselective substitutions at either the alpha- or gamma-allenic position. A specific synthetic application of the novel alpha-substituted allenamides in intramolecular Pauson-Khand-type cycloadditions is also described here.

Entities:  

Year:  2000        PMID： 10964386     DOI： 10.1021/ol000181+

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


  11 in total

1.  A tandem 1,3-H-shift-6π-electrocyclization-cyclic 2-amido-diene intramolecular Diels-Alder cycloaddition approach to BCD-Ring of atropurpuran.

Authors:  Ryuji Hayashi; Zhi-Xiong Ma; Richard P Hsung
Journal:  Org Lett       Date:  2011-12-13       Impact factor: 6.005

2.  Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.

Authors:  Ryuji Hayashi; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

3.  Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

4.  Thermal intramolecular [4 + 2] cycloadditions of allenamides: a stereoselective tandem propargyl amide isomerization-cycloaddition.

Authors:  Andrew G Lohse; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

5.  Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)-H functionalisation.

Authors:  Yue Xia; Nicholas W Wade; Philip N Palermo; Yidong Wang; Yi-Ming Wang
Journal:  Chem Commun (Camb)       Date:  2021-12-09       Impact factor: 6.222

6.  Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction.

Authors:  Francois Grillet; Kay M Brummond
Journal:  J Org Chem       Date:  2013-03-29       Impact factor: 4.354

7.  Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Authors:  Ryuji Hayashi; Richard P Hsung; John B Feltenberger; Andrew G Lohse
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

8.  Synthesis of amido-spiro[2.2]pentanes via Simmons-Smith cyclopropanation of allenamides.

Authors:  Ting Lu; Ryuji Hayashi; Richard P Hsung; Kyle A DeKorver; Andrew G Lohse; Zhenlei Song; Yu Tang
Journal:  Org Biomol Chem       Date:  2009-06-19       Impact factor: 3.876

Review 9.  Allenamides: a powerful and versatile building block in organic synthesis.

Authors:  Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2013-04-04       Impact factor: 60.622

10.  An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors:  Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883
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