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Synfacts 2019; 15(02): 0149
DOI: 10.1055/s-0037-1611985
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective α-Functionalization of Ketones

Contributor(s):
Paul Knochel
,
Moritz Balkenhohl
He Z.-T, Hartwig JF. * University of California, Berkeley, USA
Enantioselective α-Functionalizations of Ketones via Allylic Substitution of Silyl Enol Ethers.

Nat. Chem. 2018;
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Publication History

Publication Date:
18 January 2019 (online)

 
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Key words

enantioselectivity - iridium catalysis - ketones

Significance

Hartwig and He developed an efficient and enantioselective method for the α-functionalization of ketones by performing iridium-catalyzed allylic substitutions on silyl enol ethers.


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Comment

The yields and enantio- or diastereoselectivities of this method are exceptionally high, making this protocol extremely useful for the synthesis of enantiomerically pure α-substituted ketones. Additionally, not only N-, but also S-, O-, or C-nucleophiles were applicable to this method.


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