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 languageEnglish
Pages (from-to)18593–18600
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number51
Early online date11 Nov 2016
DOIs
Publication statusPublished - 19 Dec 2016

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