Literature DB >> 12603105

A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides.

Michael O Frederick1, Jason A Mulder, Michael R Tracey, Richard P Hsung, Jian Huang, Kimberly C M Kurtz, Lichun Shen, Christopher J Douglas.   

Abstract

A class="Chemical">copper-catalyzed new C-N bond formation involving a class="Chemical">sp-hybridized <class="Chemical">span class="Chemical">carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.

Entities:  

Year:  2003        PMID： 12603105     DOI： 10.1021/ja021304j

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


  30 in total

Review 1.  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

2.  Direct palladium-catalyzed alkynylation of N-fused heterocycles.

Authors:  Ilya V Seregin; Victoria Ryabova; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

3.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  A unique approach to aldol products for the creation of all-carbon quaternary stereocentres.

Authors:  Jaya Prakash Das; Helena Chechik; Ilan Marek
Journal:  Nat Chem       Date:  2009-03-29       Impact factor: 24.427

5.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

6.  Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors:  Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-10-28       Impact factor: 4.354

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.  Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes.

Authors:  Joshua R Dunetz; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

9.  Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.

Authors:  Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-09-03       Impact factor: 4.354

10.  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
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