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Literature DB >> 17845052

Electronic effects in the pt-catalyzed cycloisomerization of propargylic esters: synthesis of 2,3-disubstituted indolizines as a mechanistic probe.

Abstract

The initial 5-exo versus 6-endo cyclization of the acyl group onto the activated alkyne of propargylic esters has been found to be dependent on electronic effects of the acyl, alkyne, and propargylic carbon substituents. These electronic effects control the ratio of 2,3-disubstituted versus 1,3-disubstituted indolizine products formed when substrates bearing pyridines at the alkyne terminus are used.

Entities: Chemical

Year: 2007 PMID： 17845052 PMCID： PMC3342703 DOI： 10.1021/ol701973s

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

18 in total

1. A novel 1,2-migration of acyloxy, phosphatyloxy, and sulfonyloxy groups in allenes: efficient synthesis of tri- and tetrasubstituted furans.

Authors: Anna W Sromek; Alexander V Kel'in; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2004-04-19 Impact factor: 15.336

2. Propargylic esters in gold catalysis: access to diversity.

Authors: Nicolas Marion; Steven P Nolan
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors: B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal: J Am Chem Soc Date: 2005-09-14 Impact factor: 15.419

4. A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles.

Authors: A V Kel'in; A W Sromek; V Gevorgyan
Journal: J Am Chem Soc Date: 2001-03-07 Impact factor: 15.419

5. Au(I)-catalyzed cycloisomerization of 1,5-enynes bearing a propargylic acetate: formation of unexpected bicyclo[3.1.0]hexene.

Authors: Nicolas Marion; Pierre de Frémont; Gilles Lemière; Edwin D Stevens; Louis Fensterbank; Max Malacria; Steven P Nolan
Journal: Chem Commun (Camb) Date: 2006-04-13 Impact factor: 6.222

6. Reactivity and selectivity of 1,3-diyn-6-enes in electrophilic transition metal-catalyzed reactions.

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

7. Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes.

Authors: Victor Mamane; Tobias Gress; Helga Krause; Alois Fürstner
Journal: J Am Chem Soc Date: 2004-07-21 Impact factor: 15.419

8. Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors: Koji Miki; Kouichi Ohe; Sakae Uemura
Journal: J Org Chem Date: 2003-10-31 Impact factor: 4.354

9. 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

10. Palladium-catalyzed arylation and heteroarylation of indolizines.

Authors: Choul-Hong Park; Victoria Ryabova; Ilya V Seregin; Anna W Sromek; Vladimir Gevorgyan
Journal: Org Lett Date: 2004-04-01 Impact factor: 6.005

13 in total

1. Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors: Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Aldrichimica Acta Date: 2010 Impact factor: 3.667

2. Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles.

Authors: Dmitri Chernyak; Surendra Babu Gadamsetty; Vladimir Gevorgyan
Journal: Org Lett Date: 2008-05-08 Impact factor: 6.005

3. ORGANOCOPPER-MEDIATED TWO-COMPONENT S_N2'-SUBSTITUTION CASCADE TOWARDS N-FUSED HETEROCYCLES.

Authors: D Chernyak; V Gevorgyan
Journal: Chem Heterocycl Compd (N Y) Date: 2012-03-01 Impact factor: 1.277

4. Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: access to polycyclic N-fused heterocycles.

Authors: Dmitri Chernyak; Vladimir Gevorgyan
Journal: Org Lett Date: 2010-11-08 Impact factor: 6.005

5. Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines.

Authors: Alison R Hardin Narayan; Richmond Sarpong
Journal: Green Chem Date: 2010 Impact factor: 10.182

6. Two-component approach toward a fully substituted N-fused pyrrole ring.

Authors: Dmitri Chernyak; Cathy Skontos; Vladimir Gevorgyan
Journal: Org Lett Date: 2010-07-16 Impact factor: 6.005

7. Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

Authors: Stephen T Heller; Toshihiro Kiho; Alison R H Narayan; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2013-09-05 Impact factor: 15.336

8. On the validity of Au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines.

Authors: Yuanzhi Xia; Alexander S Dudnik; Yahong Li; Vladimir Gevorgyan
Journal: Org Lett Date: 2010-11-11 Impact factor: 6.005

9. C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide.

Authors: Paul A Vadola; Dalibor Sames
Journal: J Am Chem Soc Date: 2009-11-18 Impact factor: 15.419

10. Palladium-catalyzed carbonylative cyclization/arylation cascade for 2-aroylindolizine synthesis.

Authors: Zhou Li; Dmitri Chernyak; Vladimir Gevorgyan
Journal: Org Lett Date: 2012-11-28 Impact factor: 6.005