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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

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Department:
University of Oxford
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Author
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Department:
University of Oxford
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Author
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Department:
University of Oxford
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Name:
Engineering and Physical Sciences Research Council
Grant:
EP/H003711/1
Publisher:
CSIRO Publishing
Journal:
Australian Journal of Chemistry More from this journal
Volume:
68
Issue:
3
Pages:
401-403
Publication date:
2014-11-21
Acceptance date:
2014-10-15
DOI:
EISSN:
1445-0038
ISSN:
0004-9425
UUID:
uuid:c972b9f4-4e5d-4621-8a27-56fcdbcfb107
Deposit date:
2015-09-15

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