Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
Abstract
To date, effective nickel-catalyzed enantioselective cross-couplings of alkyl electrophiles that bear oxygen leaving groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents. In this Communication, we establish that, in the presence of a nickel/pybox catalyst, a variety of racemic propargylic carbonates are suitable partners for asymmetric couplings with organozinc reagents. The method is compatible with an array of functional groups and utilizes commercially available catalyst components. The development of a versatile nickel-catalyzed enantioselective cross-coupling process for electrophiles that bear a leaving group other than a halide adds a significant new dimension to the scope of these reactions.
Additional Information
© 2012 American Chemical Society. Received: January 2, 2012. Published: February 1, 2012. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM62871) and the Alexander von Humboldt Foundation (research fellowship for A.J.O.). We thank Dr. Wataru Muramatsu for a preliminary investigation. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms-354532.pdf
Supplemental Material - ja300031w_si_001.pdf
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Additional details
- PMCID
- PMC3288265
- Eprint ID
- 102851
- Resolver ID
- CaltechAUTHORS:20200428-095145561
- NIH
- R01-GM62871
- Alexander von Humboldt Foundation
- Created
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2020-04-29Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field