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Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones

Abstract:

Synthetic methods for the selective formation of all carbon quaternary centres in non-cyclic systems are rare. Here we report highly enantioselective Cu-catalytic asymmetric conjugate addition of alkylzirconium species to twelve different acyclic trisubstituted enones. A variety of sp(3)-hybridized nucleophiles generated by in situ hydrozirconation of alkenes with the Schwartz reagent can be introduced, giving linear products bearing quaternary centres with up to 98% ee. The method is toleran...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c6sc02811j

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Institution:
University of Oxford
Oxford college:
Keble College
Role:
Author
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Funding agency for:
Fletcher, S
Grant:
EP/H003711/1/
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Science Journal website
Volume:
8
Issue:
1
Pages:
641-646
Publication date:
2016-09-02
Acceptance date:
2016-09-01
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Source identifiers:
670818
Language:
English
Keywords:
Pubs id:
pubs:670818
UUID:
uuid:8e9d7732-e40d-43b6-aa23-557264a368af
Local pid:
pubs:670818
Deposit date:
2017-06-02

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