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Lewis acid catalysis alters the shapes and products of bis-pericyclic Diels-Alder transition states.

作者信息

Celebi-Olçüm Nihan, Ess Daniel H, Aviyente Viktorya, Houk K N

机构信息

Department of Chemistry and Biochemistry, University of California-Los Angeles, CA 90095-1569, USA.

出版信息

J Am Chem Soc. 2007 Apr 18;129(15):4528-9. doi: 10.1021/ja070686w. Epub 2007 Mar 27.

DOI:10.1021/ja070686w

PMID:17385868

Abstract

摘要

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Lewis acid catalysis alters the shapes and products of bis-pericyclic Diels-Alder transition states.

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Lewis acid catalysis alters the shapes and products of bis-pericyclic Diels-Alder transition states.

作者信息

Celebi-Olçüm Nihan, Ess Daniel H, Aviyente Viktorya, Houk K N

机构信息

Department of Chemistry and Biochemistry, University of California-Los Angeles, CA 90095-1569, USA.

出版信息

J Am Chem Soc. 2007 Apr 18;129(15):4528-9. doi: 10.1021/ja070686w. Epub 2007 Mar 27.

DOI:10.1021/ja070686w

PMID:17385868

Abstract

摘要

相似文献

Lewis acid catalysis alters the shapes and products of bis-pericyclic Diels-Alder transition states.

J Am Chem Soc. 2007 Apr 18;129(15):4528-9. doi: 10.1021/ja070686w. Epub 2007 Mar 27.

Effect of Lewis acid catalysts on Diels-Alder and hetero-Diels-Alder cycloadditions sharing a common transition state.

J Org Chem. 2008 Oct 3;73(19):7472-80. doi: 10.1021/jo801076t. Epub 2008 Sep 10.

Probing the Lewis acid-catalyzed intramolecular Diels-Alder cyclizations of allylic alkoxy-substituted (Z)-1,3-dienes.

Org Lett. 2003 Nov 27;5(24):4725-8. doi: 10.1021/ol035900+.

Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines.

Angew Chem Int Ed Engl. 2006 Jul 17;45(29):4796-8. doi: 10.1002/anie.200601345.

Stereoselective synthesis of 3,4-disubstituted and 3,4,5-trisubstituted piperidines by Lewis acid-catalysed ene cyclisation of 4-aza-1,7-dienes.

Org Biomol Chem. 2007 Sep 21;5(18):2925-31. doi: 10.1039/b708139a. Epub 2007 Aug 3.

Regioselective and asymmetric Diels-Alder reaction of 1- and 2-substituted cyclopentadienes catalyzed by a Brønsted acid activated chiral oxazaborolidine.

J Am Chem Soc. 2007 Aug 8;129(31):9536-7. doi: 10.1021/ja0735958. Epub 2007 Jul 14.

Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions.

Org Biomol Chem. 2004 Sep 7;2(17):2451-60. doi: 10.1039/B407293F. Epub 2004 Aug 9.

Oxazaborolidinone-catalyzed enantioselective Diels-Alder reaction of acyclic alpha,beta-unsaturated ketones.

J Org Chem. 2008 Jan 4;73(1):212-8. doi: 10.1021/jo702043g. Epub 2007 Dec 6.

Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions.

Angew Chem Int Ed Engl. 2005 Feb 25;44(10):1484-7. doi: 10.1002/anie.200461319.

Heteropoly acid-catalyzed microwave-assisted three-component aza-Diels-Alder cyclizations: diastereoselective synthesis of potential drug candidates for Alzheimer's disease.

Org Biomol Chem. 2011 Mar 7;9(5):1394-401. doi: 10.1039/c0ob00638f. Epub 2011 Jan 5.

引用本文的文献

Catalyst-controlled regiodivergence and stereodivergence in formal cross-[4+2] cycloadditions: The unique effect of bismuth(III).

Sci Adv. 2025 Mar 28;11(13):eadt5997. doi: 10.1126/sciadv.adt5997. Epub 2025 Mar 26.

Interplay between Energy and Entropy Mediates Ambimodal Selectivity of Cycloadditions.

J Chem Theory Comput. 2024 Dec 24;20(24):10942-10951. doi: 10.1021/acs.jctc.4c01138. Epub 2024 Dec 6.

Total Synthesis and Prediction of Ulodione Natural Products Guided by DFT Calculations.

Angew Chem Int Ed Engl. 2022 Aug 8;61(32):e202207004. doi: 10.1002/anie.202207004. Epub 2022 Jun 28.

Prediction of the [4 + 2]- and [5 + 4]-cycloaddition reactions in zig-zag carbon nanotubes an ambimodal transition state: density functional theory calculations.

RSC Adv. 2020 Mar 17;10(19):11111-11120. doi: 10.1039/c9ra10252c. eCollection 2020 Mar 16.

Bifurcating reactions: distribution of products from energy distribution in a shared reactive mode.

Chem Sci. 2021 Aug 23;12(38):12682-12694. doi: 10.1039/d1sc02826j. eCollection 2021 Oct 6.

Computational Exploration of the Mechanism of Critical Steps in the Biomimetic Synthesis of Preuisolactone A, and Discovery of New Ambimodal (5 + 2)/(4 + 2) Cycloadditions.

J Am Chem Soc. 2021 May 5;143(17):6601-6608. doi: 10.1021/jacs.1c01856. Epub 2021 Apr 22.

The [4+2]-Cycloaddition of α-Nitrosoalkenes with Thiochalcones as a Prototype of Periselective Hetero-Diels-Alder Reactions-Experimental and Computational Studies.

Chemistry. 2020 Jan 2;26(1):237-248. doi: 10.1002/chem.201903385. Epub 2019 Nov 22.

Understanding the Molecular Mechanism of the Rearrangement of Internal Nitronic Ester into Nitronorbornene in Light of the MEDT Study.

Molecules. 2019 Jan 28;24(3):462. doi: 10.3390/molecules24030462.

Biosynthesis of Grandione: An Example of Tandem Hetero Diels-Alder/Retro-Claisen Rearrangement Reaction?

Molecules. 2018 Sep 30;23(10):2505. doi: 10.3390/molecules23102505.

Sequential Diels-Alder/[3,3]-sigmatropic rearrangement reactions of β-nitrostyrene with 3-methyl-1,3-pentadiene.

Beilstein J Org Chem. 2013 Oct 17;9:2137-46. doi: 10.3762/bjoc.9.251. eCollection 2013.