Literature DB >> 20337418

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

Kyle A Dekorver1, Richard P Hsung, Andrew G Lohse, Yu Zhang.   

Abstract

A fascinating mechanistic study of ynamido-palladium-pi-allyl complexes is described that features isolation of a unique silyl ketenimine via aza-Claisen rearrangement, which can be accompanied by an unusual thermal N-to-C 1,3-Ts shift in the formation of tertiary nitriles and a novel cyclopentenimine formation via a palladium-catalyzed aza-Rautenstrauch-type cyclization pathway.

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Year:  2010        PMID： 20337418      PMCID： PMC2862050          DOI： 10.1021/ol100446p

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


  35 in total

1.  First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant.

Authors:  Carole Alayrac; Dieter Schollmeyer; Bernhard Witulski
Journal:  Chem Commun (Camb)       Date:  2009-02-18       Impact factor: 6.222

2.  Atropisomerism of alpha,beta-unsaturated amidines: stereoselective synthesis by catalytic cascade reaction and optical resolution.

Authors:  Naoya Shindoh; Yoshiji Takemoto; Kiyosei Takasu
Journal:  Chemistry       Date:  2009-07-20       Impact factor: 5.236

3.  Creating aldols differently: how to build up aldol products with quaternary stereocenters starting from alkynes.

Authors:  Dennis C Koester; Daniel B Werz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams.

Authors:  Lawrence L W Cheung; Andrei K Yudin
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

5.  Synthesis of tricyclic fused 3-aminopyridines through intramolecular Co(I)-catalyzed [2+2+2] cycloaddition between ynamides, nitriles, and alkynes.

Authors:  Pierre Garcia; Solenne Moulin; Yves Miclo; David Leboeuf; Vincent Gandon; Corinne Aubert; Max Malacria
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

6.  Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes.

Authors:  Alexis Coste; François Couty; Gwilherm Evano
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

7.  Cationic cyclopentannelation of allene ethers.

Authors:  Marcus A Tius
Journal:  Acc Chem Res       Date:  2003-04       Impact factor: 22.384

8.  Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides.

Authors:  Benoit Gourdet; Mairi E Rudkin; Ciorsdaidh A Watts; Hon Wai Lam
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.

Authors:  Xiaohua Huang; Kevin W Anderson; Danilo Zim; Lei Jiang; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2003-06-04       Impact factor: 15.419

10.  Application of ynamides in the synthesis of 2-amidoindoles.

Authors:  Karin Dooleweerdt; Thomas Ruhland; Troels Skrydstrup
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005
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  15 in total

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

Authors:  Kyle A DeKorver; Richard P Hsung; Wang-Ze Song; Xiao-Na Wang; Mary C Walton
Journal:  Org Lett       Date:  2012-06-05       Impact factor: 6.005

2.  A serendipitous discovery: nickel catalyst for the cycloaddition of diynes with unactivated nitriles.

Authors:  Puneet Kumar; Simon Prescher; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-20       Impact factor: 15.336

3.  An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors:  Kyle A Dekorver; Troy D North; Richard P Hsung
Journal:  Synlett       Date:  2010-10       Impact factor: 2.454

Review 4.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

5.  Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2012-01-24       Impact factor: 6.005

6.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

7.  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

8.  Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

Authors:  Xing-zhong Shu; Suyu Huang; Dongxu Shu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

9.  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

10.  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
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