Literature DB >> 12098261

The first successful base-promoted isomerization of propargyl amides to chiral ynamides. Applications in ring-closing metathesis of ene-ynamides and tandem RCM of diene-ynamides.

Jian Huang1, Hui Xiong, Richard P Hsung, C Rameshkumar, Jason A Mulder, Tyler P Grebe.   

Abstract

[reaction: see text] A highly useful sequence of reactions is described here. These reactions consist of the first successful base-induced isomerizations of propargyl amides to chiral ynamides, applications of these novel ynamides in ring-closure metathesis leading to chiral 2-amidodienes useful for Diels-Alder cycloadditions, and the first successful tandem RCM of diene-ynamides.

Entities:  

Year:  2002        PMID： 12098261     DOI： 10.1021/ol020097p

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


  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.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

Review 3.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

4.  Intramolecular Cyclization Strategies Toward the Synthesis of Zoanthamine Alkaloids.

Authors:  Derek Fischer; Thong X Nguyen; Lynnie Trzoss; Marianna Dakanali; Emmanuel A Theodorakis
Journal:  Tetrahedron Lett       Date:  2011-09-21       Impact factor: 2.415

5.  SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors:  Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal:  Organic Synth       Date:  2007

6.  Synthesis of the entire framework of tartrolon B utilizing a silicon-tethered ring-closing metathesis strategy.

Authors:  Yi Jin Kim; Daesung Lee
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

7.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

Review 8.  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

9.  Application of tandem ring-closing enyne metathesis: formal total synthesis of (-)-cochleamycin A.

Authors:  Sumit Mukherjee; Daesung Lee
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

10.  Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides.

Authors:  Joshua R Dunetz; Rick L Danheiser
Journal:  Org Lett       Date:  2003-10-16       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.