Chirality Transfer in Gold (I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes

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Abstract: Gold (I)‐catalysed intermolecular hydroalkoxylation of enantioenriched 1,3‐disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemisation. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported here, exploiting conditions that suppress allene racemisation. A full substrate scope study reveals that excellent regio‐ and stereoselectivities are achieved when a σ‐withdrawing substituent is present.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Chirality Transfer in Gold (I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes ; volume:22 ; number:51 ; year:2016 ; pages:18593-18600 ; extent:8
Chemistry - a European journal ; 22, Heft 51 (2016), 18593-18600 (gesamt 8)

Creator: Webster, Stacey
Sutherland, Daniel R.
Lee, Ai‐Lan

DOI: 10.1002/chem.201603918

URN: urn:nbn:de:101:1-2022101407073547089896

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:27 AM CEST

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Webster, Stacey
Sutherland, Daniel R.
Lee, Ai‐Lan

Other Objects (12)

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Hochschulschrift

Manganese- and cobalt-catalysed (transfer) hydrogenations

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Hochschulschrift

Manganese- and cobalt-catalysed (transfer) hydrogenations

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Hochschulschrift

Manganese- and cobalt-catalysed (transfer) hydrogenations

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

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Chirality Transfer in Gold (I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes

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Other Objects (12)

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Manganese- and cobalt-catalysed (transfer) hydrogenations

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Manganese- and cobalt-catalysed (transfer) hydrogenations

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Manganese- and cobalt-catalysed (transfer) hydrogenations

Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

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