Lundgren, Rylan J. and Wilsily, Ashraf and Marion, Nicolas and Ma, Cong and Chung, Ying Kit and Fu, Gregory C. (2013) Catalytic Asymmetric C-N Bond Formation: Phosphine-Catalyzed Intra- and Intermolecular γ-Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates. Angewandte Chemie International Edition, 52 (9). pp. 2525-2528. ISSN 1433-7851. PMCID PMC3819219. doi:10.1002/anie.201208957. https://resolver.caltech.edu/CaltechAUTHORS:20130326-080903622
![[img]](https://authors.library.caltech.edu/style/images/fileicons/application_pdf.png) |
PDF
- Accepted Version
See Usage Policy. 1MB | |
|
PDF
- Supplemental Material
See Usage Policy. 1MB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20130326-080903622
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.
| Item Type: | Article | ||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Related URLs: |
| ||||||||||||||
| ORCID: |
| ||||||||||||||
| 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. | ||||||||||||||
| Funders: |
| ||||||||||||||
| Subject Keywords: | amination; asymmetric catalysis; heterocycles; organocatalysis; phosphanes | ||||||||||||||
| Issue or Number: | 9 | ||||||||||||||
| PubMed Central ID: | PMC3819219 | ||||||||||||||
| DOI: | 10.1002/anie.201208957 | ||||||||||||||
| Record Number: | CaltechAUTHORS:20130326-080903622 | ||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130326-080903622 | ||||||||||||||
| Official Citation: | Lundgren, R. J., Wilsily, A., Marion, N., Ma, C., Chung, Y. K. and Fu, G. C. (2013), Catalytic Asymmetric CN Bond Formation: Phosphine-Catalyzed Intra- and Intermolecular γ-Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates . Angew. Chem. Int. Ed., 52: 2525–2528. doi: 10.1002/anie.201208957 | ||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
| ID Code: | 37620 | ||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||||
| Deposited On: | 26 Mar 2013 23:12 | ||||||||||||||
| Last Modified: | 09 Nov 2021 23:30 |
Repository Staff Only: item control page
