Published October 14, 2009
| Accepted Version + Supplemental Material
Journal Article
Open
Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes
- Creators
- Smith, Sean W.
-
Fu, Gregory C.
Abstract
A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ functionalization of carbonyl (and related) compounds.
Additional Information
© 2009 American Chemical Society. Received August 4, 2009. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM57034), Merck Research Laboratories, and Novartis. We thank Dr. Nicolas Marion for assistance, Evonik Degussa for providing samples of phosphepines 1−4, and Prof. Qi-Lin Zhou for providing a precursor to phosphine 5. Funding for the MIT Department of Chemistry Instrumentation Facility has been furnished in part by NIH IS10RR13886 and NSF DBI-9729592.Attached Files
Accepted Version - nihms147483.pdf
Supplemental Material - ja9061823_si_001.pdf
Files
ja9061823_si_001.pdf
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Additional details
- PMCID
- PMC2758928
- Eprint ID
- 102867
- DOI
- 10.1021/ja9061823
- Resolver ID
- CaltechAUTHORS:20200428-095147086
- R01-GM57034
- NIH
- Merck Research Laboratories
- Novartis
- IS10RR13886
- NIH
- DBI-9729592
- NSF
- Created
-
2020-04-28Created from EPrint's datestamp field
- Updated
-
2021-11-16Created from EPrint's last_modified field