Literature DB >> 22667819

An intramolecular [2 + 2] cycloaddition of ketenimines via palladium-catalyzed rearrangements of N-allyl-ynamides.

Kyle A DeKorver1, Richard P Hsung, Wang-Ze Song, Xiao-Na Wang, Mary C Walton.   

Abstract

A cascade of Pd-catalyzed N-to-C allyl transfer-intramolecular ketenimine-[2 + 2] cycloadditions of N-allyl ynamides is described. This tandem sequence is highly stereoselective and the [2 + 2] cycloaddition could be rendered in a crossed or fused manner depending on alkene substitutions, leading to bridged and fused bicycloimines.

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Year:  2012        PMID： 22667819      PMCID： PMC3426664          DOI： 10.1021/ol3013233

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


  16 in total

1.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

Review 2.  Cu-catalyzed azide-alkyne cycloaddition.

Authors:  Morten Meldal; Christian Wenzel Tornøe
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

3.  Synthesis of aminopyridines and aminopyridones by cobalt-catalyzed [2+2+2] cycloadditions involving yne-ynamides: scope, limitations, and mechanistic insights.

Authors:  Pierre Garcia; Yannick Evanno; Pascal George; Mireille Sevrin; Gino Ricci; Max Malacria; Corinne Aubert; Vincent Gandon
Journal:  Chemistry       Date:  2012-03-01       Impact factor: 5.236

4.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

5.  Intramolecular [2 + 2] cycloaddition reactions of alkynyl ether derived ketenes. A convenient synthesis of donor-acceptor cyclobutanes.

Authors:  Vincent Tran; Thomas G Minehan
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

6.  Total synthesis of (-)-herbindoles A, B, and C via transition-metal-catalyzed intramolecular [2 + 2 + 2] cyclization between ynamide and diynes.

Authors:  Nozomi Saito; Taisuke Ichimaru; Yoshihiro Sato
Journal:  Org Lett       Date:  2012-03-27       Impact factor: 6.005

7.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       Impact factor: 6.005

8.  Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.

Authors:  Kyle A DeKorver; Mary C Walton; Troy D North; Richard P Hsung
Journal:  Org Lett       Date:  2011-08-17       Impact factor: 6.005

9.  Competition between alkenes in intramolecular ketene-alkene [2 + 2] cycloaddition: what does it take to win?

Authors:  Guillaume Bélanger; François Lévesque; Julie Pâquet; Guillaume Barbe
Journal:  J Org Chem       Date:  2005-01-07       Impact factor: 4.354

10.  Synthesis of amidines using N-allyl ynamides. A palladium-catalyzed allyl transfer through an ynamido-pi-allyl complex.

Authors:  Yu Zhang; Kyle A DeKorver; Andrew G Lohse; Yan-Shi Zhang; Jian Huang; Richard P Hsung
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005
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  6 in total

1.  SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

Authors:  Xiao-Na Wang; Richard P Hsung; Sierra K Fox; Ming-Can Lv; Rui Qi
Journal:  Heterocycles       Date:  2014-01-01       Impact factor: 0.831

2.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

3.  Ynamides in ring forming transformations.

Authors:  Xiao-Na Wang; Hyun-Suk Yeom; Li-Chao Fang; Shuzhong He; Zhi-Xiong Ma; Brant L Kedrowski; Richard P Hsung
Journal:  Acc Chem Res       Date:  2013-10-28       Impact factor: 22.384

4.  A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.

Authors:  Xiao-Na Wang; Richard P Hsung; Rui Qi; Sierra K Fox; Ming-Can Lv
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

5.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157

6.  Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides.

Authors:  Holly V Adcock; Elli Chatzopoulou; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-30       Impact factor: 15.336
  6 in total

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