Published February 25, 2013
| Version Accepted Version + Supplemental Material
Journal Article
Open
Catalytic Asymmetric C-N Bond Formation: Phosphine-Catalyzed Intra- and Intermolecular γ-Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates
Creators
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1.
California Institute of Technology
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2.
Massachusetts Institute of Technology
Abstract
Pin the amine on the gamma: A new method has been developed for the γ-addition of nitrogen nucleophiles to γ-substituted alkynoates or allenoates through intra- and intermolecular processes that are catalyzed by spirophosphine 1 (see scheme). An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,β-unsaturated carbonyl compounds.
Additional Information
© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: November 8, 2012; Published online: January 21, 2013. This research has been supported by the National Institutes of Health (National Institute of General Medical Sciences: R01- GM57034), the Natural Sciences and Engineering Research Council of Canada (postdoctoral fellowship for R.J.L.), the Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique DCSO, F91128 Palaiseau, France (fellowship for C.M.), and the Croucher Foundation (postdoctoral fellowship for Y.K.C.). We thank Shoshana Bachman for a preliminary study.Attached Files
Accepted Version - nihms521614.pdf
Supplemental Material - anie_201208957_sm_miscellaneous_information.pdf
Files
anie_201208957_sm_miscellaneous_information.pdf
Additional details
Identifiers
- PMCID
- PMC3819219
- Eprint ID
- 37620
- Resolver ID
- CaltechAUTHORS:20130326-080903622
Funding
- NIH
- R01-GM57034
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Laboratoire de Synthèse Organique
- Centre National de la Recherche Scientifique (CNRS)
- UMR 7652
- Ecole Polytechnique DCSO
- Croucher Foundation
Dates
- Created
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2013-03-26Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field