Literature DB >> 18937407

Synthesis of alpha-keto-imides via oxidation of ynamides.

Ziyad F Al-Rashid1, Whitney L Johnson, Richard P Hsung, Yonggang Wei, Pei-Yuan Yao, Renhei Liu, Kang Zhao.   

Abstract

A de novo preparation of alpha-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of alpha-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarbonyl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides.

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Year:  2008        PMID： 18937407      PMCID： PMC2720040          DOI： 10.1021/jo8015067

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  38 in total

1.  Ruthenium-catalyzed [2 + 2] cycloadditions of ynamides.

Authors:  Nicole Riddell; Karine Villeneuve; William Tam
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

2.  A strategy for the synthesis of aryl alpha-ketoamides based upon the acylation of anions derived from cyanomethylamines followed by oxidative cleavage.

Authors:  Zhong Yang; Zhongxing Zhang; Nicholas A Meanwell; John F Kadow; Tao Wang
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

3.  An expeditious synthesis of DPD and boron binding studies.

Authors:  Martin F Semmelhack; Shawn R Campagna; Michael J Federle; Bonnie L Bassler
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

4.  Alpha-diketone and alpha-keto ester derivatives of N-protected amino acids and peptides as novel inhibitors of cysteine and serine proteinases.

Authors:  M R Angelastro; S Mehdi; J P Burkhart; N P Peet; P Bey
Journal:  J Med Chem       Date:  1990-01       Impact factor: 7.446

5.  Peptide alpha-keto ester, alpha-keto amide, and alpha-keto acid inhibitors of calpains and other cysteine proteases.

Authors:  Z Li; G S Patil; Z E Golubski; H Hori; K Tehrani; J E Foreman; D D Eveleth; R T Bartus; J C Powers
Journal:  J Med Chem       Date:  1993-10-29       Impact factor: 7.446

6.  A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.

Authors:  Xuejun Zhang; Richard P Hsung; Hongyan Li; Yu Zhang; Whitney L Johnson; Ruth Figueroa
Journal:  Org Lett       Date:  2008-07-10       Impact factor: 6.005

7.  Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation.

Authors:  Ziyad F Al-Rashid; Richard P Hsung
Journal:  Org Lett       Date:  2008-01-17       Impact factor: 6.005

8.  Synthesis of functionalized oxazolones by a sequence of Cu(II)- and Au(I)-catalyzed transformations.

Authors:  Florin M Istrate; Andrea K Buzas; Igor Dias Jurberg; Yann Odabachian; Fabien Gagosz
Journal:  Org Lett       Date:  2008-02-02       Impact factor: 6.005

9.  A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

Authors:  Pei-Yuan Yao; Yu Zhang; Richard P Hsung; Kang Zhao
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

10.  A triazole-templated ring-closing metathesis for constructing novel fused and bridged triazoles.

Authors:  Xuejun Zhang; Richard P Hsung; Hongyan Li
Journal:  Chem Commun (Camb)       Date:  2007-06-21       Impact factor: 6.222
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  12 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.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

3.  Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2017-10-16       Impact factor: 54.564

4.  Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

5.  A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Authors:  Hongyan Li; Jennifer E Antoline; Jin-Haek Yang; Ziyad F Al-Rashid; Richard P Hsung
Journal:  New J Chem       Date:  2010-01-01       Impact factor: 3.591

6.  Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Authors:  Renhe Liu; Gabrielle N Winston-McPherson; Zhong-Yue Yang; Xin Zhou; Wangze Song; Ilia A Guzei; Xiufang Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419

7.  An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2016-02-02       Impact factor: 4.354

8.  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

9.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Ruth Figueroa; Ryuji Hayashi; Richard P Hsung
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

10.  Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles.

Authors:  Dong-Mei Cui; Dan-Wen Zhuang; Ying Chen; Chen Zhang
Journal:  Beilstein J Org Chem       Date:  2011-06-24       Impact factor: 2.883
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