Published October 5, 2011
| Accepted Version + Supplemental Material
Journal Article
Open
Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
- Creators
- Zultanski, Susan L.
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Fu, Gregory C.
Abstract
With the aid of a chiral nickel catalyst, enantioselective γ- (and δ-) alkylations of carbonyl compounds can be achieved through the coupling of γ-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon–halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon–carbon bond formation.
Additional Information
© 2011 American Chemical Society. Received: August 22, 2011. Published: September 13, 2011. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), a Merck Summer Fellowship (S.L.Z.), and a Robert T. Haslam Graduate Fellowship (S.L.Z.).Attached Files
Accepted Version - nihms324923.pdf
Supplemental Material - ja2079515_si_001.cif
Supplemental Material - ja2079515_si_002.pdf
Files
nihms324923.pdf
Additional details
- PMCID
- PMC3183125
- Eprint ID
- 102852
- Resolver ID
- CaltechAUTHORS:20200428-095145670
- NIH
- R01-GM62871
- Merck
- Massachusetts Institute of Technology (MIT)
- Created
-
2020-04-29Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field