KOtBu‐Mediated Domino Isomerization and Functionalization of Aromatic Allylic Alcohols

Transition‐metal‐ as well as ligand‐free base‐mediated domino isomerization and alkylation of allylic alcohols is presented. This protocol features the conversion of simple allylic alcohols into the corresponding ketones through isomerization in the presence of a simple base. Significantly, these in...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-07, Vol.2017 (26), p.3886-3895
Main Authors: Suchand, Basuli, Satyanarayana, Gedu
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Alkylation
Allylic compounds
Domino reactions
Hydrogen transfer
Isomerization
Ketones
Styrenes
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Description
Summary:Transition‐metal‐ as well as ligand‐free base‐mediated domino isomerization and alkylation of allylic alcohols is presented. This protocol features the conversion of simple allylic alcohols into the corresponding ketones through isomerization in the presence of a simple base. Significantly, these in situ generated ketones subsequently undergo alkylation with styrenes as electrophiles, in a domino one‐pot fashion, as an atom‐ and step‐economical chemical process. A simple KOtBu‐mediated synthesis of functionalized ketones through domino internal hydrogen transfer and functionalization of allylic alcohols is reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700440