Site- and Enantioselective Formation of Allene-Bearing Tertiary or Quaternary Carbon Stereogenic Centers through NHC–Cu-Catalyzed Allylic Substitution

Catalytic enantioselective allylic substitutions that result in addition of an allenyl group (98% SN2′ selectivity, and 99:1 enantiomeric ratio (er). Site-selective NHC–Cu-catalyzed hydroboration of enantiomerically enriched allenes and conversion to the corresponding β-vinyl ketones demonstrates th...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-01, Vol.134 (3), p.1490-1493
Main Authors: Jung, Byunghyuck, Hoveyda, Amir H
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Allyl Compounds - chemistry
Carbon - chemistry
Catalysis
Copper - chemistry
Methane - analogs & derivatives
Methane - chemistry
Stereoisomerism
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Summary:Catalytic enantioselective allylic substitutions that result in addition of an allenyl group (98% SN2′ selectivity, and 99:1 enantiomeric ratio (er). Site-selective NHC–Cu-catalyzed hydroboration of enantiomerically enriched allenes and conversion to the corresponding β-vinyl ketones demonstrates the method's utility.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja211269w