以强酸性手性布朗斯特酸作为高效催化剂的高度对映选择性有机催化羰基-烯反应。 - Suppr

Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

作者信息

Rueping Magnus, Theissmann Thomas, Kuenkel Alexander, Koenigs René M

机构信息

Degussa Endowed Professorship, Institute for Organic Chemistry and Chemical Biology, Johann Wolfgang Goethe University, Max-von-Laue Strasse 7, 60438 Frankfurt am Main, Germany.

出版信息

Angew Chem Int Ed Engl. 2008;47(36):6798-801. doi: 10.1002/anie.200802139.

DOI:10.1002/anie.200802139

PMID:18655079

Abstract

摘要

相似文献

Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

Angew Chem Int Ed Engl. 2008;47(36):6798-801. doi: 10.1002/anie.200802139.

Chiral Brønsted acids in enantioselective carbonyl activations--activation modes and applications.

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Pyridinium 1,1'-binaphthyl-2,2'-disulfonates as highly effective chiral Brønsted acid-base combined salt catalysts for enantioselective Mannich-type reaction.

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Modulating the acidity: highly acidic Brønsted acids in asymmetric catalysis.

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Chiral Brønsted acids in the catalytic asymmetric Nazarov cyclization--the first enantioselective organocatalytic electrocyclic reaction.

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Design of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction.

J Am Chem Soc. 2006 Aug 2;128(30):9626-7. doi: 10.1021/ja062508t.

Asymmetric Brønsted acid catalyzed carbonyl activation--organocatalytic domino electrocyclization-halogenation reaction.

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Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions.

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引用本文的文献

Domino dehydration/intermolecular (enantioselective) ketone-ene reactions catalysed by a simple solid in batch and in flow.

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Dual-Hydrogen-Bond Donor and Brønsted Acid Cocatalysis Enables Highly Enantioselective Protio-Semipinacol Rearrangement Reactions.

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Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures.

Molecules. 2021 Jan 12;26(2):355. doi: 10.3390/molecules26020355.

FBINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes.

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Chiral Brønsted acid-catalyzed intramolecular S2' reaction for enantioselective construction of a quaternary stereogenic center.

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Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc.

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Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

作者信息

Rueping Magnus, Theissmann Thomas, Kuenkel Alexander, Koenigs René M

机构信息

Degussa Endowed Professorship, Institute for Organic Chemistry and Chemical Biology, Johann Wolfgang Goethe University, Max-von-Laue Strasse 7, 60438 Frankfurt am Main, Germany.

出版信息

Angew Chem Int Ed Engl. 2008;47(36):6798-801. doi: 10.1002/anie.200802139.

DOI:10.1002/anie.200802139

PMID:18655079

Abstract

摘要

相似文献

Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

Angew Chem Int Ed Engl. 2008;47(36):6798-801. doi: 10.1002/anie.200802139.

Chiral Brønsted acids in enantioselective carbonyl activations--activation modes and applications.

Chem Soc Rev. 2011 Sep;40(9):4539-49. doi: 10.1039/c1cs15087a. Epub 2011 May 25.

Pyridinium 1,1'-binaphthyl-2,2'-disulfonates as highly effective chiral Brønsted acid-base combined salt catalysts for enantioselective Mannich-type reaction.

J Am Chem Soc. 2008 Dec 17;130(50):16858-60. doi: 10.1021/ja806875c.

Modulating the acidity: highly acidic Brønsted acids in asymmetric catalysis.

Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6706-20. doi: 10.1002/anie.201100169. Epub 2011 Jun 15.

Chiral Brønsted acids in the catalytic asymmetric Nazarov cyclization--the first enantioselective organocatalytic electrocyclic reaction.

Angew Chem Int Ed Engl. 2007;46(12):2097-100. doi: 10.1002/anie.200604809.

Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Brønsted acid catalyzed self-coupling of enamides.

Chem Commun (Camb). 2008 Oct 14(38):4637-9. doi: 10.1039/b804477e. Epub 2008 Aug 5.

Design of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction.

J Am Chem Soc. 2006 Aug 2;128(30):9626-7. doi: 10.1021/ja062508t.

Asymmetric Brønsted acid catalyzed carbonyl activation--organocatalytic domino electrocyclization-halogenation reaction.

Chem Commun (Camb). 2011 Nov 7;47(41):11450-2. doi: 10.1039/c1cc15289k. Epub 2011 Sep 5.

Chiral arylaminophosphonium barfates as a new class of charged brønsted acid for the enantioselective activation of nonionic Lewis bases.

J Am Chem Soc. 2009 Jun 3;131(21):7242-3. doi: 10.1021/ja903271t.

Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions.

Chem Commun (Camb). 2008 Sep 21(35):4097-112. doi: 10.1039/b807577h. Epub 2008 Jul 11.

引用本文的文献

Domino dehydration/intermolecular (enantioselective) ketone-ene reactions catalysed by a simple solid in batch and in flow.

RSC Adv. 2024 Oct 18;14(45):32944-32957. doi: 10.1039/d4ra06449f. eCollection 2024 Oct 17.

Dual-Hydrogen-Bond Donor and Brønsted Acid Cocatalysis Enables Highly Enantioselective Protio-Semipinacol Rearrangement Reactions.

J Am Chem Soc. 2023 Jul 19;145(28):15036-15042. doi: 10.1021/jacs.3c02960. Epub 2023 Jul 10.

Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.

J Am Chem Soc. 2021 Dec 8;143(48):20077-20083. doi: 10.1021/jacs.1c10890. Epub 2021 Nov 23.

A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.

J Am Chem Soc. 2021 Jun 30;143(25):9585-9594. doi: 10.1021/jacs.1c03992. Epub 2021 Jun 21.

Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures.

Molecules. 2021 Jan 12;26(2):355. doi: 10.3390/molecules26020355.

FBINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes.

Chem Sci. 2018 Nov 19;10(5):1426-1433. doi: 10.1039/c8sc03587c. eCollection 2019 Feb 7.

Chiral Brønsted acid-catalyzed intramolecular S2' reaction for enantioselective construction of a quaternary stereogenic center.

Chem Sci. 2018 Jun 5;9(26):5747-5757. doi: 10.1039/c8sc01942h. eCollection 2018 Jul 14.

Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc.

Beilstein J Org Chem. 2018 Mar 7;14:576-582. doi: 10.3762/bjoc.14.44. eCollection 2018.

The effect of host structure on the selectivity and mechanism of supramolecular catalysis of Prins cyclizations.

Chem Sci. 2015 Feb 1;6(2):1383-1393. doi: 10.1039/c4sc02735c. Epub 2014 Nov 28.

Chem Sci. 2015 Aug 1;6(8):4912-4922. doi: 10.1039/c5sc01614b. Epub 2015 Jun 2.

Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

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Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

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