Multifunctionalized 3-hydroxypyrroles in a Three-step, One-pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2011 Oct 29

PMID 22032199

Citations 16

Authors

Xinfang Xu

Maxim O Ratnikov

Peter Y Zavalij

Michael P Doyle

Affiliations

Soon will be listed here.

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).

Citing Articles

B(CF)-Catalyzed Diastereoselective and Divergent Reactions of Vinyldiazo Esters with Nitrones: Synthesis of Highly Functionalized Diazo Compounds.

Stefkova K, Guerzoni M, van Ingen Y, Richards E, Melen R Org Lett. 2023; 25(3):500-505.

PMID: 36634071 PMC: 9887602. DOI: 10.1021/acs.orglett.2c04198.

Application of vinylogous carbamates and vinylogous aminonitriles to the regiospecific synthesis of uniquely functionalized pyrroles and quinolones.

Gupton J, Crawford E, Mahoney M, Clark E, Curry W, Lane A Tetrahedron. 2019; 74(52):7408-7420.

PMID: 31289413 PMC: 6615762. DOI: 10.1016/j.tet.2018.10.078.

Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Tan W, Yoshikai N Chem Sci. 2018; 6(11):6448-6455.

PMID: 30090263 PMC: 6054072. DOI: 10.1039/c5sc02322j.

Cycloaddition reactions of enoldiazo compounds.

Cheng Q, Deng Y, Lankelma M, Doyle M Chem Soc Rev. 2017; 46(17):5425-5443.

PMID: 28726896 PMC: 5575991. DOI: 10.1039/c7cs00324b.

The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Xu X, Doyle M Acc Chem Res. 2014; 47(4):1396-405.

PMID: 24650430 PMC: 3993878. DOI: 10.1021/ar5000055.

References

Davis F, Wu Y, Xu H, Zhang J . Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and delta-amino beta-ketophosphonates. Org Lett. 2004; 6(24):4523-5. DOI: 10.1021/ol048157+. View

Doyle M, Kundu K, Russell A . Catalytic addition methods for the synthesis of functionalized diazoacetoacetates and application to the construction of highly substituted cyclobutanones. Org Lett. 2005; 7(23):5171-4. DOI: 10.1021/ol052003s. View

Truong P, Xu X, Doyle M . An efficient methodology to substituted furans via oxidation of functionalized α-diazo-β-ketoacetates. Tetrahedron Lett. 2011; 52(17):2093-2096. PMC: 3080702. DOI: 10.1016/j.tetlet.2010.11.166. View

Zhang X, Richter L, DeLongchamp D, Kline R, Hammond M, McCulloch I . Molecular packing of high-mobility diketo pyrrolo-pyrrole polymer semiconductors with branched alkyl side chains. J Am Chem Soc. 2011; 133(38):15073-84. DOI: 10.1021/ja204515s. View

Wang H, Mueller D, Sachwani R, Kapadia R, Londino H, Anderson L . Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes. J Org Chem. 2011; 76(9):3203-21. DOI: 10.1021/jo200061b. View

Lubriks D, Sokolovs I, Suna E . Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles. Org Lett. 2011; 13(16):4324-7. DOI: 10.1021/ol201665c. View

Kuk Kim S, Sessler J, Gross D, Lee C, Kim J, Lynch V . A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes. J Am Chem Soc. 2010; 132(16):5827-36. DOI: 10.1021/ja100715e. View

Wang J, Stefane B, Jaber D, Smith J, Vickery C, Diop M . Remote C-H functionalization: using the N-O moiety as an atom-economical tether to obtain 1,5- and the rare 1,7-C-H insertions. Angew Chem Int Ed Engl. 2010; 49(23):3964-8. DOI: 10.1002/anie.201000160. View

Rakshit S, Patureau F, Glorius F . Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes. J Am Chem Soc. 2010; 132(28):9585-7. DOI: 10.1021/ja104305s. View

10.

Baughman R . Materials science. Playing nature's game with artificial muscles. Science. 2005; 308(5718):63-5. DOI: 10.1126/science.1099010. View

11.

Merz A, Anikin S, Lieser B, Heinze J, John H . 3,3'- and 4,4'-Dimethoxy-2,2'-bipyrroles: highly electron-rich model compounds for polypyrrole formation. Chemistry. 2003; 9(2):449-55. DOI: 10.1002/chem.200390047. View

12.

Seiple I, Su S, Young I, Nakamura A, Yamaguchi J, Jorgensen L . Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines. J Am Chem Soc. 2011; 133(37):14710-26. PMC: 3173569. DOI: 10.1021/ja2047232. View

13.

Attanasi O, Favi G, Mantellini F, Moscatelli G, Santeusanio S . Synthesis of functionalized pyrroles via catalyst- and solvent-free sequential three-component enamine-azoene annulation. J Org Chem. 2011; 76(8):2860-6. DOI: 10.1021/jo200287k. View

14.

Merino P, Jimenez P, Tejero T . Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone. J Org Chem. 2006; 71(12):4685-8. DOI: 10.1021/jo060465t. View

15.

Wang X, Xu X, Zavalij P, Doyle M . Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates. J Am Chem Soc. 2011; 133(41):16402-5. PMC: 3192303. DOI: 10.1021/ja207664r. View

16.

Thompson B, Montgomery J . Enone-alkyne reductive coupling: a versatile entry to substituted pyrroles. Org Lett. 2011; 13(13):3289-91. DOI: 10.1021/ol201133n. View

17.

Yamagishi M, Nishigai K, Hata T, Urabe H . Nucleophilic addition of sulfonamides to bromoacetylenes: facile preparation of pyrroles. Org Lett. 2011; 13(18):4873-5. DOI: 10.1021/ol201952b. View

18.

Fan H, Peng J, Hamann M, Hu J . Lamellarins and related pyrrole-derived alkaloids from marine organisms. Chem Rev. 2007; 108(1):264-87. PMC: 4928200. DOI: 10.1021/cr078199m. View

19.

Trost B, Lumb J, Azzarelli J . An atom-economic synthesis of nitrogen heterocycles from alkynes. J Am Chem Soc. 2010; 133(4):740-3. PMC: 3043142. DOI: 10.1021/ja110117g. View

20.

Wang Y, Zhu S . Convenient synthesis of polyfunctionalized beta-fluoropyrroles from rhodium(II)-catalyzed intramolecular N-H insertion reactions. Org Lett. 2003; 5(5):745-8. DOI: 10.1021/ol0275670. View