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Literature DB >> 22032199

Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Xinfang Xu¹, Maxim O Ratnikov, Peter Y Zavalij, Michael P Doyle.

Abstract

The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).

Entities: Chemical Disease Species

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Year: 2011 PMID： 22032199 PMCID： PMC3223024 DOI： 10.1021/ol2026125

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

23 in total

1. An efficient methodology to substituted furans via oxidation of functionalized α-diazo-β-ketoacetates.

Authors: Phong Truong; Xinfang Xu; Michael P Doyle
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

2. A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes.

Authors: Sung Kuk Kim; Jonathan L Sessler; Dustin E Gross; Chang-Hee Lee; Jong Seung Kim; Vincent M Lynch; Laetitia H Delmau; Benjamin P Hay
Journal: J Am Chem Soc Date: 2010-04-28 Impact factor: 15.419

3. Materials science. Playing nature's game with artificial muscles.

Authors: Ray H Baughman
Journal: Science Date: 2005-04-01 Impact factor: 47.728

4. Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.

Authors: Souvik Rakshit; Frederic W Patureau; Frank Glorius
Journal: J Am Chem Soc Date: 2010-07-21 Impact factor: 15.419

5. Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors: Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal: J Am Chem Soc Date: 2011-08-23 Impact factor: 15.419

6. Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone.

Authors: Pedro Merino; Pablo Jimenez; Tomas Tejero
Journal: J Org Chem Date: 2006-06-09 Impact factor: 4.354

7. Catalytic addition methods for the synthesis of functionalized diazoacetoacetates and application to the construction of highly substituted cyclobutanones.

Authors: Michael P Doyle; Kousik Kundu; Albert E Russell
Journal: Org Lett Date: 2005-11-10 Impact factor: 6.005

8. Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles.

Authors: Dmitrijs Lubriks; Igors Sokolovs; Edgars Suna
Journal: Org Lett Date: 2011-07-20 Impact factor: 6.005

9. Efficient route to 4H-1,3-oxazines through ring expansion of isoxazoles by rhodium carbenoids.

Authors: James R Manning; Huw M L Davies
Journal: Tetrahedron Date: 2008-01-14 Impact factor: 2.457

10. Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and delta-amino beta-ketophosphonates.

Authors: Franklin A Davis; Yongzhong Wu; He Xu; Junyi Zhang
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

14 in total

1. 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

2. Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors: Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal: Angew Chem Int Ed Engl Date: 2013-10-02 Impact factor: 15.336

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. Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Authors: Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal: Angew Chem Int Ed Engl Date: 2012-07-16 Impact factor: 15.336

5. Substrate-dependent divergent outcomes from catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides: azabicyclo[3.1.0]hexanes or 5-arylaminofuran-2(3H)-ones.

Authors: Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal: J Org Chem Date: 2012-06-04 Impact factor: 4.354

6. Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: synthesis of highly functionalized cyclopentanones.

Authors: Phong Truong; Charles S Shanahan; Michael P Doyle
Journal: Org Lett Date: 2012-06-28 Impact factor: 6.005

10. Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors: Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal: J Am Chem Soc Date: 2013-01-17 Impact factor: 15.419