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

Stacey Webster; Daniel R. Sutherland; Ai-Lan Lee

doi:10.1002/chem.201603918

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

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

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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.

Original language	English
Pages (from-to)	18593–18600
Number of pages	8
Journal	Chemistry - A European Journal
Volume	22
Issue number	51
Early online date	11 Nov 2016
DOIs	https://doi.org/10.1002/chem.201603918
Publication status	Published - 19 Dec 2016

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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.",

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AU - Sutherland, Daniel R.

AU - Lee, Ai-Lan

N1 - ◦"Hot Paper" as judged by referees ◦Highlighted on ChemistryViews website

PY - 2016/12/19

Y1 - 2016/12/19

N2 - 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.

AB - 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.

U2 - 10.1002/chem.201603918

DO - 10.1002/chem.201603918

M3 - Article

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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ER -

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

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