Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.
作者信息
Çelebi-Ölçüm Nihan, Lam Yu-hong, Richmond Edward, Ling Kenneth B, Smith Andrew D, Houk Kendall N
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.
出版信息
Angew Chem Int Ed Engl. 2011 Nov 25;50(48):11478-82. doi: 10.1002/anie.201105412. Epub 2011 Oct 4.
Abstract
摘要
相似文献
1
Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.
Angew Chem Int Ed Engl. 2011 Nov 25;50(48):11478-82. doi: 10.1002/anie.201105412. Epub 2011 Oct 4.
2
Asymmetric pericyclic cascade approach to spirocyclic oxindoles.
Org Lett. 2012 Jun 1;14(11):2762-5. doi: 10.1021/ol300982f. Epub 2012 May 14.
3
Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.
Angew Chem Int Ed Engl. 2012 Mar 5;51(10):2448-51. doi: 10.1002/anie.201107417. Epub 2012 Jan 27.
4
An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations.
Org Biomol Chem. 2015 Feb 14;13(6):1807-17. doi: 10.1039/c4ob02526a.
5
Asymmetric Synthesis of 3-Spiro-Fused 2-Oxindoles via Organocatalyst/N-Iodosuccinimide/Hydrogen Peroxide-Mediated Oxidative Cyclization.
Chem Pharm Bull (Tokyo). 2025;73(4):382-387. doi: 10.1248/cpb.c24-00839.
6
Iron trichloride-promoted cyclization of o-alkynylaryl isocyanates: synthesis of 3-(chloromethylene)oxindoles.
Org Lett. 2009 Oct 1;11(19):4262-5. doi: 10.1021/ol9014877.
7
FeCl3-Mediated Radical Tandem Reactions of 3-Benzyl-2-oxindoles with Styrene Derivatives for the Stereoselective Synthesis of Spirocyclohexene Oxindoles.
Org Lett. 2016 Mar 18;18(6):1382-5. doi: 10.1021/acs.orglett.6b00234. Epub 2016 Mar 7.
8
Assembly of spirooxindole derivatives containing four consecutive stereocenters via organocatalytic Michael-Henry cascade reactions.
Org Lett. 2012 Apr 6;14(7):1834-7. doi: 10.1021/ol300441z. Epub 2012 Mar 22.
9
Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates.
Org Lett. 2015 Nov 6;17(21):5508-11. doi: 10.1021/acs.orglett.5b02929. Epub 2015 Oct 29.
10
Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.
ACS Comb Sci. 2012 Apr 9;14(4):285-93. doi: 10.1021/co300003c. Epub 2012 Apr 2.
引用本文的文献
1
Mechanistic duality of indolyl 1,3-heteroatom transposition.
Chem Sci. 2023 Jun 16;14(28):7688-7698. doi: 10.1039/d3sc00716b. eCollection 2023 Jul 19.
2
Oxindole synthesis polar-radical crossover of ketene-derived amide enolates in a formal [3 + 2] cycloaddition.
Chem Sci. 2022 Mar 9;13(13):3875-3879. doi: 10.1039/d1sc07134c. eCollection 2022 Mar 30.
3
Stereoselective Synthesis of (4,5)-5-Vinyloxazolidin-2-one-4-carboxylate as a β-Vinylserine Synthetic Equivalent by Vinyl Grignard Addition to an -Tosyl Version of Garner's Aldehyde.
Synlett. 2021;32(6):601-604. doi: 10.1055/a-1308-0370. Epub 2020 Nov 10.
4
Elucidating the origin of selectivity of [3 + 2]-cycloaddition reactions between thioketone and carbohydrate-derived nitrones by the DFT.
J Mol Model. 2019 Jul 2;25(7):209. doi: 10.1007/s00894-019-4104-6.
5
Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.
J Org Chem. 2017 Oct 20;82(20):10875-10882. doi: 10.1021/acs.joc.7b01521. Epub 2017 Sep 28.
本文引用的文献
1
Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.
Chem Rev. 2011 Aug 10;111(8):5042-137. doi: 10.1021/cr100212h. Epub 2011 Jun 28.
2
Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst.
Nat Chem. 2011 Jun;3(6):473-7. doi: 10.1038/nchem.1039. Epub 2011 May 8.
3
Cascade polycyclisations in natural product synthesis.
Org Biomol Chem. 2011 Jun 7;9(11):3997-4006. doi: 10.1039/c1ob05212h. Epub 2011 Apr 28.
4
Why do some Fischer indolizations fail?
J Am Chem Soc. 2011 Apr 20;133(15):5752-5. doi: 10.1021/ja201035b. Epub 2011 Mar 28.
5
Unraveling the mechanism of cascade reactions of zincke aldehydes.
J Am Chem Soc. 2011 Mar 23;133(11):3895-905. doi: 10.1021/ja107988b. Epub 2011 Feb 25.
6
Organocatalytic cascade reactions as a new tool in total synthesis.
Nat Chem. 2010 Mar;2(3):167-78. doi: 10.1038/nchem.539. Epub 2010 Feb 19.
7
Fast oxy-cope rearrangements of bis-alkynes: competition with central C-C bond fragmentation and incorporation in tunable cascades diverging from a common bis-allenic intermediate.
J Org Chem. 2010 Dec 17;75(24):8689-92. doi: 10.1021/jo101838a. Epub 2010 Nov 23.
8
The development of endo-selective epoxide-opening cascades in water.
Chem Soc Rev. 2009 Nov;38(11):3175-92. doi: 10.1039/b816697h. Epub 2009 Sep 16.
9
[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products.
Chem Soc Rev. 2009 Nov;38(11):3133-48. doi: 10.1039/b901177n. Epub 2009 Sep 2.
10
Pericyclic domino reactions: concise approaches to natural carbocyclic frameworks.
Chem Soc Rev. 2009 Nov;38(11):3092-101. doi: 10.1039/b819798a. Epub 2009 Jul 10.
Zotero 插件