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Asymmetric remote C-H functionalization: use of internal olefins in tandem hydrometallation-isomerization-asymmetric conjugate addition sequences

Abstract:

We describe catalytic asymmetric C-C formation using terminal alkyl-metal nucleophiles generated from internal olefins through a 'chain-walking' isomerization mechanism. Hydrometallation of internal olefins with the Schwartz reagent gives the least hindered alkyl-zirconocene after thermal (60°C in THF) isomerization. After switching the solvent from THF to dichloromethane, the alkyl-zirconocenes can be used in copper-catalyzed asymmetric conjugate additions. Addition to a variety of cyclic α,...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1071/CH14556

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More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Publisher:
CSIRO Publishing Publisher's website
Journal:
Australian Journal of Chemistry Journal website
Volume:
68
Issue:
3
Pages:
401-403
Publication date:
2015-01-01
DOI:
EISSN:
1445-0038
ISSN:
0004-9425
URN:
uuid:2a6a8651-d9cf-4ca5-829d-a892805c65e0
Source identifiers:
516557
Local pid:
pubs:516557

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