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

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, ex...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-12, Vol.22 (51), p.18593-18600
Main Authors: Webster, Stacey, Sutherland, Daniel R., Lee, Ai-Lan
Format: Article
Language:English
Subjects:
alcohols
Allene
allenes
Chemistry
Chirality
chirality transfer
ether
gold
Racemization
Stereoselectivity
Substrates
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Summary: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. Gold(I)‐catalyzed intermolecular hydroalkoxylation of enantioenriched 1,3‐disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemization. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported, exploiting conditions that suppress allene racemization. Excellent regio‐ and stereoselectivities are achieved when a slightly σ‐withdrawing substituent is present.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201603918